Ammonium Chloride → HCID 15117210, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trimethylsilylacetylene (17 ml) in tetrahydrofuran (100 ml) were added successively a solution of n-butyllithium in n-hexane (1.50M, 81 ml) and a solution of 1-acetyl-4-piperidone (11.5 g) in tetrahydrofuran (15 ml) at -78° C. After stirring at -78° C. for 30 minutes, to the mixture was added acetic acid (5.0 ml) and the resultant mixture was taken up into a mixture of aqueous ammonium chloride (300 ml) and ethyl acetate (300 ml) at 0° C. The organic layer was separated and washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave a crystalline which was collected by filtration, and washed with n-hexane to give 1-acetyl-4-hydroxy-4-(2-trimethylsilylethynyl)piperidine (14.48 g).

Provenance & Evidence