Hydrochloric Acid → HCID 67148556, compound

Participants

Reaction Conditions

Reaction Steps

Treat a −78° C. solution of 4-(tert-butyl-diphenyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (21.22 g, 51.7 mmol) in THF (200 mL) with a 2M solution of lithium diisopropylamide in heptane/THF/ethylbenzene (31 mL, 62.0 mmol) and stir at −78° C. for 15 minutes under N2. Warm the reaction to −20° C. and then re-cool to −78° C. Treat the reaction with bromoacetonitrile (9.30 g, 77.5 mmol) and stir at −78° C. for 1 hour. Warm the reaction to room temperature and stir 1 hour. Acidify the reaction with 1 N HCl, dilute with ethyl acetate, and wash with water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product that is purified with a 0 to 20% ethyl acetate in hexanes gradient on silica gel to afford 10.96 g (47%) of the titled product. Rf=0.25 and 0.21 (5/1 hexanes/ethyl acetate). MS (m/z): 450 (M+).

Provenance & Evidence