Ethyl Propionate → HCID 68453922, compound

Participants

Reaction Steps

A solution of (1S,5R)-6,6-dimethyl-bicyclo[3.1.0]hexan-3-one (2.0 g, 16.1 mmol, step f above) in THF (20 mL) is treated with K. tert.-butylate (1.99 g, 17.7 mmol). The dark brown solution is stirred at rt for 30 min before ethyl propionate (18.5 mL, 161 mmol) is added. Stirring is continued at rt for 1 h. The mixture is diluted with 10% aq. citric acid and extracted with diethyl ether. The organic extract is washed with brine, dried over NaSO4 and the solvent is evaporated to leave rac-(1S,5R)-6,6-dimethyl-2-propionyl-bicyclo[3.1.0]hexan-3-one (2.35 g) as a brown oil. LC-MS: tR=0.99 min, [M+1]+=181.29, 1H NMR (CDCl3): δ 2.64 (dd, J=7.6, 20.0 Hz, 1H), 2.36-2.22 (m, 3H), 1.75 (d, J=7.6 Hz, 1H), 1.30-1.22 (m, 1H), 1.18 (t, J=7.6 Hz, 3H), 1.10 (s, 3H), 0.82 (s, 3H).

Provenance & Evidence