反应详情

温度

100 °C

0.700 g (1.42 mmol) of 3-benzyloxypropyl)triphenylphosphonium bromide, 0.305 g (1.18 mmol) of trans-(4-formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester (example 1.2) and 0.662 g of finely milled potassium carbonate were suspended in 10.0 ml of 2-methyl-2-butanol and the reaction mixture intensively stirred at 100° C. for 2 hours. It was then evaporated, poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and ether as the eluent giving 0.364 g (78.6%) trans-[4-(4-benzyloxy-[E/Z 1:9]but-1-enyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 331 [M−C4H8)+].

1. customIt was then evaporated
2. additionpoured into 50 ml of an ice/water mixture
3. extractionextracted 3 times with 50 ml of ethylacetate
4. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
5. customevaporated under reduced pressure
6. customThe residue formed
7. customwas chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and ether as the eluent