Potassium Cyanide → α-Methyl-α-[(trimethylsilyl)oxy]cyclopropaneacetonitrile

Participants

Reaction Conditions

Reaction Steps

To a well stirred mixture of cyclopropylmethylketone (27.8 mL, 0.3 mol), trimethylsilylcyanide (55.8 mL, 0.45 mol) and 18-crown-6 (4.87 g, 18.5 mmol) was added potassium cyanide (2.44 g, 37.5 mmol). The temperature rose to ˜100° C. and stirring was continued for 1 h with heating to 145° C. After cooling the mixture was purified by silica gel chromatography (500 g silica, heptane/ethylacetate 6:1) to yield 47.1 g of the title compound as light brown oil, 1H NMR (CDCl3): 0.23 (s, 9H), 0.56 (m, 4H), 1.17 (m, 1H), 1.63 (s, 3H, CH3).

Provenance & Evidence