Acetic Acid → HCID 66748801, compound

Participants

Reaction Conditions

Reaction Steps

HMDS (69.6 g, 0.43 mol) was added dropwise to 350 mL of acetic acid at ambient temp over 5 minutes. Cyclopentanone (20.3 g, 0.29 mol) and ethyl cyanoacetate (65.0 g, 0.57 mol) were added in single portions to the resulting solution. The mixture was stirred at 70° C. overnight after which it was cooled to ambient temperature and the reacting mixture was poured into 600 mL of water, and extracted with ethyl acetate (500 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by flash chromatography (petroleum ether: ethyl acetate=10:1) to give the title compound as a yellow solid (37.0 g, 0.22 mol, 77.2%). LC-MS: m/e=166.2 (M+H+).

Provenance & Evidence