Cyclohexanol → HCID 86600139, compound

Participants

Reaction Steps

To a stirred solution of methyl 5-hydroxynicotinate (2.40 g, 15.7 mmol) in methylene chloride (40 mL) was added cyclohexanol (1.73 g, 1.80 mL, 17.2 mmol) and triphenylphosphine (5.75 g, 21.9 mmol). The solution was treated with diethyl azodicarboxylate (3.20 mL, 20.4 mmol), resulting in a mild exotherm and development of an orange colored solution. The reaction mixture was allowed to stir at room temperature. After 16 hours, the cloudy yellow suspension was filtered, and the filtrate was washed with saturated sodium bicarbonate solution and brine, dried (magnesium sulfate), filtered, and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.08 g (29%) of the desired product as a colorless oil: 1H NMR (CDCl3) δ 8.77 (d, J=1.7 Hz, 1H), 8.43 (d, J=2.9 Hz, 1H), 7.74 (dd, J=1.7, 2.9 Hz, 1H), 4.37-4.31 (m, 1H), 3.94 (s, 3H), 2.01-1.93 (m, 2H), 1.85-1.75 (m, 2H), 1.62-1.49 (m, 3H), 1.46-1.31 (m, 3H) ppm. 13C NMR (CDCl3) δ 166.2, 154.0, 144.2, 142.9, 126.6, 122.3, 76.3, 52.7, 31.6, 25.6, 23.7 ppm.

Provenance & Evidence