GB2156351A - An ester - Google Patents

An ester Download PDF

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Publication number
GB2156351A
GB2156351A GB08510717A GB8510717A GB2156351A GB 2156351 A GB2156351 A GB 2156351A GB 08510717 A GB08510717 A GB 08510717A GB 8510717 A GB8510717 A GB 8510717A GB 2156351 A GB2156351 A GB 2156351A
Authority
GB
United Kingdom
Prior art keywords
methyl
ethyl
ester
formyl
pentadienoate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB08510717A
Other versions
GB8510717D0 (en
GB2156351B (en
Inventor
Ernst Peter Krebs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB8510717D0 publication Critical patent/GB8510717D0/en
Publication of GB2156351A publication Critical patent/GB2156351A/en
Application granted granted Critical
Publication of GB2156351B publication Critical patent/GB2156351B/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/74—Unsaturated compounds containing —CHO groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

This invention provides ethyl (all-E)-5-formyl-4-methyl-2,4-pentadienoate which is useful as an intermediate for the manufacture of pharmaceutically valuable polyene compounds which form the subject of copending Application No. 8317129.

Description

1
GB 2 156 351 A 1
SPECIFICATION An ester
5 The present invention is concerned with an ester. The ester provided by the invention is ethyl (all-E)- 5-formyl-4-methyl-2,4-pentadienoate.
The above ester is useful as an intermediate for the manufacture of pharmaceutically valuable po-10 lyene compounds which form the subject of our copending Application No 8317129.
Ethyl (all-E)-5-formyl-4-methyl-2,4-pentadienoate can be prepared as follows:
(a) 43.23 g of triethyl phosphonoacetate are 15 added to 4.63 g of sodium hydride in 100 ml of dry tetrahydrofuran. 25.0 g (0.18 mol) of 7-acetoxy-tiglic aldehyde in 50 ml of tetrahydrofuran are subsequently added dropwise at 0-5°C. The mixture is stirred at room temperature for 20 hours, diluted 20 with 200 ml of ethyl acetate, washed with saturated sodium chloride solution and dried over magnesium sulphate. Concentration and distillation at 103°C/0.35 mmHg give 28.6 g (76%) of ethyl 6-acetoxy-4-methyl-2,4-hexadienoate.
25 (b) 27.5 g of ethyl 6-acetoxy-4-methyl-2,4-hexadi-enoate, 20 g of sodium carbonate and 2 ml of tri-ethanolamine are heated to reflux for 3 hours in 250 ml of ethanol. After the addition of ethyl acetate, the organic phase is washed with saturated 30 sodium chloride solution, dried over magnesium sulphate and concentrated. Distillation at 110°C/0.4 mmHg give 15.7 g (71%) of ethyl 6-hydroxy-4-methyl-2,4-hexadienoate.
(c) 11.7 g of ethyl 6-hydroxy-4-methyl-2,4-hexadi-35 enoate in 200 ml of dichloromethane are stirred at room temperature for 4 hours with 30 g manganese (IV) oxide. The solution is filtered and concentrated and the residue is then recrystallized from hexane-cyclohexane. There are obtained 9.1 g 40 (78%) of ethyl 5-formyl-4- methyl-2,4-pentadi-enoate of melting point 48-49°C.

Claims (1)

  1. 45 Ethyl (all-E)-5-formyl-4-methyl-2,4-pentadienoate.
    Printed in the UK for HMSO, D8818935, 8/85, 7102.
    Published by The Patent Office, 25 Southampton Buildings, London,
    WC2A 1AY, from which copies may be obtained.
GB08510717A 1982-06-24 1985-04-26 An ester Expired GB2156351B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH3889/82A CH651007A5 (en) 1982-06-24 1982-06-24 POLYEN CONNECTIONS.

Publications (3)

Publication Number Publication Date
GB8510717D0 GB8510717D0 (en) 1985-06-05
GB2156351A true GB2156351A (en) 1985-10-09
GB2156351B GB2156351B (en) 1986-05-14

Family

ID=4265678

Family Applications (2)

Application Number Title Priority Date Filing Date
GB08317129A Expired GB2122200B (en) 1982-06-24 1983-06-23 Polyene compounds
GB08510717A Expired GB2156351B (en) 1982-06-24 1985-04-26 An ester

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB08317129A Expired GB2122200B (en) 1982-06-24 1983-06-23 Polyene compounds

Country Status (19)

Country Link
JP (1) JPS5910547A (en)
AT (1) AT392780B (en)
AU (1) AU560027B2 (en)
BE (1) BE897118A (en)
CA (1) CA1276032C (en)
CH (1) CH651007A5 (en)
DE (1) DE3321662A1 (en)
DK (1) DK159392C (en)
FR (1) FR2529201B1 (en)
GB (2) GB2122200B (en)
IE (1) IE55285B1 (en)
IL (1) IL69028A0 (en)
IT (1) IT1212753B (en)
LU (1) LU84870A1 (en)
NL (1) NL8302136A (en)
NZ (1) NZ204628A (en)
PH (1) PH20070A (en)
SE (1) SE454984B (en)
ZA (1) ZA834473B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1203634B (en) * 1984-08-13 1989-02-15 Oreal 1-SUBSTITUTED DERIVATIVES OF 4-METHOXY-2,3,6-TRIMETHYLBENZENE THEIR PREPARATION PROCESS AND MEDICAMENTOUS AND COSMETIC COMPOSITIONS CONTAINING THEM
FR2621912B1 (en) * 1987-10-16 1990-03-02 Oreal NOVEL NORBORNANE DERIVATIVES, THEIR PREPARATION PROCESS AND COSMETIC AND MEDICINAL COMPOSITIONS CONTAINING THEM
DE4033568A1 (en) * 1990-10-22 1992-04-23 Henkel Kgaa BICYCLIC COMPOUNDS WITH ANTISEBORRHOIC EFFECT
MX9700778A (en) * 1994-08-10 1997-05-31 Hoffmann La Roche Retinoic acid x-receptor ligands.

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1070173B (en) * 1959-12-03 Badische Anilin- S. Soda-Fabrik Aktiengesellschaft, Ludwigshafen / Rhein Process for the preparation of 13- [2 ', 6', 6'-trimethylcyclohexen- (l ') - yl- (l')] - 3,7, ll-trimethyltridecahexaene - (2,4,6,8,10, 12) - säureil) or their esters
DE923252C (en) * 1944-09-23 1955-02-07 Schering Ag Process for the preparation of a polyenecarboxylic acid of the formula CHO
AT207831B (en) * 1957-11-27 1960-02-25 Hoffmann La Roche Process for the preparation of polyenecarboxylic acid esters and their saponification products
AT222103B (en) * 1958-08-07 1962-07-10 Bayer Ag Process for the preparation of 2-trans-β-ionylideneacetic acid
CH529742A (en) * 1970-02-02 1972-10-31 Hoffmann La Roche Process for the production of vitamin A acid amides
AT340903B (en) * 1974-03-29 1978-01-10 Hoffmann La Roche PROCESS FOR PRODUCING NEW POLYENE COMPOUNDS
DE2456959A1 (en) * 1974-12-03 1976-06-16 Basf Ag 4- (E) - AND 4- (Z) -7-METHYL-9- (2,6,6TRIMETHYL-1-CYCLOHEXEN-1-YL) -NONA-2,4,6,8TETRAEN CARBONIC ACID, ITS DERIVATIVES AND CONTAINING THEM PREPARATIONS
CH624373A5 (en) * 1975-11-14 1981-07-31 Hoffmann La Roche Process for the preparation of polyene compounds
CA1111441A (en) * 1976-12-20 1981-10-27 Werner Bollag Polyene compounds
LU77254A1 (en) * 1977-05-04 1979-01-18
US4169103A (en) * 1978-04-12 1979-09-25 Hoffmann-La Roche Inc. Nonatetraenoic acid derivatives
DE2843884A1 (en) * 1978-10-07 1980-04-24 Basf Ag MEDIUM CONTAINING 2- (RETINYLIDES) - MALONIC ACID DERIVATIVES

Also Published As

Publication number Publication date
FR2529201A1 (en) 1983-12-30
AU560027B2 (en) 1987-03-26
CH651007A5 (en) 1985-08-30
FR2529201B1 (en) 1988-08-19
ATA230583A (en) 1990-11-15
GB8510717D0 (en) 1985-06-05
DK287083A (en) 1983-12-25
DK159392B (en) 1990-10-08
DK287083D0 (en) 1983-06-21
DE3321662C2 (en) 1992-11-26
GB2156351B (en) 1986-05-14
SE8303539D0 (en) 1983-06-20
AU1620183A (en) 1984-01-05
NZ204628A (en) 1985-07-31
NL8302136A (en) 1984-01-16
CA1276032C (en) 1990-11-06
GB2122200B (en) 1986-05-08
AT392780B (en) 1991-06-10
IL69028A0 (en) 1983-10-31
IT8321721A0 (en) 1983-06-21
GB2122200A (en) 1984-01-11
SE8303539L (en) 1983-12-25
BE897118A (en) 1983-12-23
DE3321662A1 (en) 1983-12-29
IE831471L (en) 1983-12-24
GB8317129D0 (en) 1983-07-27
ZA834473B (en) 1984-03-28
IT1212753B (en) 1989-11-30
PH20070A (en) 1986-09-18
JPH0441134B2 (en) 1992-07-07
IE55285B1 (en) 1990-08-01
SE454984B (en) 1988-06-13
JPS5910547A (en) 1984-01-20
DK159392C (en) 1991-03-04
LU84870A1 (en) 1985-03-29

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PCNP Patent ceased through non-payment of renewal fee