Water → HCID 178444561, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-ethylsulfonyl-1-phenyl-1H-tetrazole (5.0 g) and anhydrous ethylene glycol dimethyl ether (50 ml) at −60° C. was added 0.5 M potassium hexamethyldisilazane solution (in toluene, 19.7 ml), and the mixture was stirred for 20 minutes. Under the same condition, a solution of t-butyl trans-4-(2-formylethyl)cyclohexylcarbamate (2.65 g) (Example 73 (3)) in anhydrous ethylene glycol dimethyl ether (20 ml) was added thereto. The reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added water, and the mixture was stirred for 1 hour, then extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. 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 252 mg of t-butyl trans-4-[(E)-3-pentenyl]cyclohexylcarbamate.

Provenance & Evidence