Acetone → HCID 18449571, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (4.2 mL) in THF (30 mL) at 0° C. was added n-BuLi in hexanes (1.6 M, 19 mL). After stirring for 30 min., the reaction mixture was cooled to −78° C. and cyclohexanecarbonitrile (1.09 g, 10 mmol) in THF (10 mL) was added drop wise. After 2 h, acetone (1.16 g, 20 mmol) was added. The reaction mixture was stirred from −78° C. to rt overnight, diluted with Et2O (100 mL), washed with 1N HCl, H2O, brine and dried over anhydrous sodium sulfate. Purification by flash chromatography (1:1, hexanes-Et2O) gave 1-(1-hydroxy-1-methyl-ethyl)-cyclohexanecarbonitrile (1.27 g, 76%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ (ppm) 0.86–1.91 (8H, m), 1.35 (6H, s), 2.01 (2H, d, J=12.8 Hz), 3.65 (1H, t, J=6.4 Hz). Mass Spec [M+H]+=168.1.

Provenance & Evidence