Cyclopropyl methyl ketone → 1,3-Dicyclopropylpropane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

Sodium ethoxide (8 g, 117.64 mmol) was added to a solution of cyclopropyl methyl ketone (5 g, 59.4 mmol) and methyl cyclopropane carboxylate (12 ml, 118.9 mmol) in DMSO (30 mL). The resulting mixture was heated at 60° C. overnight and then cooled to 0° C. After quenching the reaction with 6N HCl, work-up (H2O/AcOEt) gave the title compound as a brown liquid which was used without any purification. 1H-NMR (δ ppm, CDCl3, 400 MHz): 16.05 (bs, 0.6H), 5.72 (s, 0.6H) 3.78 (s, 0.8H), 2.08-2.0 (m, 0.8H), 1.62-1.53 (m, 1.2H), 1.12-1.05 (m, 4H), 0.97-0.83 (m, 4H). MS (m/z): 153.2 [M+H]+.

Provenance & Evidence