反应详情

To a mixture of potassium t-butoxide (379 mg) and anhydrous N,N-dimethylformamide (20 ml) was added isobutyltriphenylphosphonium bromide (1.35 g) at room temperature. The mixture was stirred for 10 minutes, and then a solution of t-butyl trans-4-formylcyclohexyl-carbamate (700 mg) in N,N-dimethylformamide (3 ml) was added to the mixture. After the reaction mixture was stirred overnight, saturated aqueous ammonium chloride was added thereto. The mixture was extracted with toluene, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. After diethyl ether was added to the residue, the precipitate was filtered off and then the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 380 mg of t-butyl trans-{4-[(Z)-3-methyl-1-butenyl]cyclohexyl}-carbamate.

1. stirringAfter the reaction mixture was stirred overnight
2. extractionThe mixture was extracted with toluene
3. washthe organic layer was washed with brine
4. dry with materialdried over sodium sulfate
5. customthe solvent was removed in vacuo
6. additionAfter diethyl ether was added to the residue
7. filtrationthe precipitate was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)