N-Methoxy-N,3-dimethylbenzamide → Cyclopropyl 3-methylphenyl ketone

Participants

Reaction Steps

To a solution of N-methoxy-N,3-dimethylbenzamide (2.86 g, 16 mmol) in THF (50 mL) was added cyclopropylmagnesium bromide (2 N in THF, 40 mmol, 20 mL) dropwise at 0° C. After addition, the reaction mixture was stirred for 4 hours at room temperature and quenched with 30 mL of aqueous NH4Cl. The aqueous phase was separated and extracted with ethyl acetate (50 mL×2). The combined organic phase was washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated to give crude product as a yellow oil (2.56 g, 100%). LC-MS (M+H): m/z 161. 1H NMR (400 MHz, CDCl3): δ ppm 7.817 (s, 2H), 7.367-7.332 (m, 2H), 2.697-2.635 (m, 1H), 2.417 (s, 3H), 1.247-1.209 (m, 2H), 1.046-1.000 (m, 2H).

Provenance & Evidence