Ammonia → HCID 67114168, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7 (163 mg, 0.78 mmol) in THF (8.8 mL) was added LDA (2M solution in THF/n-heptane/ethylbenzene, 1.08 mL, 2.16 mmol) at −78° C. (in an isopropanol-dry ice bath). The mixture was allowed to reach room temperature over 20 min. To the mixture was added a cloudy solution of p-toluenesulfonyl cyanide (95%, 591 mg, 3.1 mmol) in THF (6.8 mL) at −78° C. The mixture was stirred at −78° C. for 30 min. To the reaction mixture was added saturated aqueous ammonia solution (4.5 mL) at −78° C. The mixture was allowed to reach room temperature. The mixture was acidified with 10% aqueous HCl solution. The mixture was extracted with ethyl acetate (30 mL×3). The extract was washed with saturated aqueous sodium bicarbonate solution (40 mL×2) and brine (40 mL), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give 5-methyl-2-oxo-5-((trimethylsilyl)ethynyl)cyclohexanecarbonitrile (270 mg).

Provenance & Evidence