反应详情

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-methyl-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.

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.