Trimethylsilylacetylene → HCID 69377678, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylsilyl acetylene at −78° C.(4.14 g, 0.042 mol) in THF (60 mL) was treated with n-butyl lithium (29 mL, 0.042 mol; 1.6 M solution in THF). The resulting mixture was stirred at −78° C. for 15 min. A solution of N-4-Boc-aminocyclohexanone (3 g, 0.014 mol; Astatech, Inc) in THF (120 mL) was added dropwise over a period of 30 min. The resulting mixture was stirred at −78° C. for 1 h and then allowed to slowly warm up to room temperature over 1 h. The reaction was quenched with a saturated solution of ammonium chloride and diluted with EtOAc and washed with saturated aqueous NaHCO3 solution, H2O, and saturated aqueous NaCl solution. The organic layer was dried over MgSO4 and concentrated to yield an off-white foam (4.38 g, 100%).

Provenance & Evidence