Tetrahydrofuran → trans-3,7-Dimethyl-9-(3-methyl-5-methoxy-2-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester

HRID 904470Notes

Reaction equation

HRID 904470 reaction equation
[Cl-].[CH3:2][C:3]1[CH:7]=[C:6]([O:8][CH3:9])[S:5][C:4]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:30]([O:32][C:33](=[O:44])[CH:34]=[C:35]([CH3:43])[CH:36]=[CH:37][CH:38]=[C:39]([CH:41]=O)[CH3:40])[CH3:31].C1OCCC1>C1(C)C=CC=CC=1>[CH2:30]([O:32][C:33](=[O:44])[CH:34]=[C:35]([CH3:43])/[CH:36]=[CH:37]/[CH:38]=[C:39]([CH3:41])[CH:40]=[CH:10][C:4]1[S:5][C:6]([O:8][CH3:9])=[CH:7][C:3]=1[CH3:2])[CH3:31]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 20285691(3-Methyl-5-methoxy-2-thenyl)triphenyl phosphonium chlorideHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoate

Product 1

HCID 131710957trans-3,7-Dimethyl-9-(3-methyl-5-methoxy-2-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5.9 g. (13.5 mmol) of (3-methyl-5-methoxy-2-thenyl)triphenyl phosphonium chloride and 2.81 g. (13.5 mmol) of ethyl-7-formyl-3-mehtyl-2,4,6-octatrienoate in 70 ml. of butylene oxide and 200 ml. of toluene was heated to 100° C. for 14 hrs. The resulting clear solution was cooled, poured into 500 ml. of a methanol/water mixture (6:4) and extracted with hexane. The combined hexane extracts were washed with methanol/water (6:4), dried and evaporated. The resulting crude, oily material was purified by chromatography (silica gel, hexane/ether, ratio 7:3) to yield after recrystallization from hexane all trans-3,7-dimethyl-9-(3-methyl-5-methoxy-2-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester, m.p. 66°-72° C.

Workup

  1. additionA suspension of 5.9 g
  2. temperatureThe resulting clear solution was cooled
  3. additionpoured into 500 ml
  4. extractionof a methanol/water mixture (6:4) and extracted with hexane
  5. washThe combined hexane extracts were washed with methanol/water (6:4)
  6. customdried
  7. customevaporated
  8. customThe resulting crude, oily material was purified by chromatography (silica gel, hexane/ether, ratio 7:3)
  9. customto yield
  10. customafter recrystallization from hexane all trans-3,7-dimethyl-9-(3-methyl-5-methoxy-2-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester, m.p. 66°-72° C.

Sources & evidence

ORD record
ord-45e9a714d5ac4fbfb7cd8fe87288df85
Source dataset
uspto-grants-1980_10
Patent number
US04230872

Reaction notes

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