Ammonium Chloride → HCID 178445700, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1.9 M sodium hexamethyldisilazane solution (in tetrahydrofuran, 2.1 ml) and anhydrous tetrahydrofuran (10 ml) was added n-propyltriphenyl-phosphonium bromide (1.52 g) at room temperature, and the mixture was stirred for 30 minutes. The reaction mixture was cooled to −78° C., and then a solution of t-butyl cis-4-formylcyclohexylcarbamate (900 mg) in anhydrous tetrahydrofuran (5 ml) was added thereto. The reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate, 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 405 mg of t-butyl cis-4-[(Z)-1-butenyl]cyclohexylcarbamate.

Provenance & Evidence