2-Cyclohexen-1-one → HCID 15934054, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of anhydrous CuCN (2.16 g, 0.025 mol) in anhydrous ether (100 mL) at -78° C. was added tert butyllithium (29.0 mL of 1.7M solution in pentane, 0.05 mol). After being stirred at -78° C. for 1 hr and at -45° C. for 30 minutes, the reaction mixture was recooled to -78° C. A solution of cyclohexenone (2.4 g,0.025 mol) in ether (25 mL) was added and stirring continued for 15 minutes at -78° C. and at -45° C. for 30 minutes. The resulting mixture was recooled to -78° C., and HMPA (10 mL) in ether (25 mL) was added. After 5 min, methyl cyanoformate (2.55 g, 0.03 mol) in ether (25 mL) was added and the reaction warmed to 0° C. over a 2 hr period. The resulting mixture was quenched with 2N HCl (100 mL), the layers were separated, and the organic phase was washed with saturated NH4Cl solution (3×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). Removal of the solvent in vacuo and purification by Kugelrohr distillation (bath temperature 100°-115° C. at 0.6 mm) afforded 4.7 g (88%) of methyl 2-(1,1-dimethylethyl)cyclohexan-6-one-carboxylate.

Provenance & Evidence