Borane → HCID 68721715, compound

Participants

Reaction Conditions

Reaction Steps

An ambient solution of oxazole (1.00 g, 14.5 mmol) and borane.tetrahydrofuran complex (14.5 mL, 14.5 mmol, 1 M in tetrahydrofuran) was stirred for 30 min. The reaction was cooled to −78° C., and n-butyllithium (9.5 mL, 15.2 mmol, 1.6 M in hexane) was added dropwise. After 30 minutes, cyclopentanone (1.42 mL, 16.0 mmol) was added dropwise. After 30 minutes, the cold (−78° C.) reaction was quenched by the addition of 5% acetic acid in ethanol (70 mL) and warmed to room temperature. The solution was diluted with diethyl ether (10 0 mL) and saturated NaHCO3 (50 mL). Layers were separated, and the organics were washed with brine (1×50 mL), dried over Na2SO4, concentrated, under reduced pressure, and purified by chromatography on SiO2 gel, eluting with 50% ethyl acetate in hexane, to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.59-1.71 (m, 2H), 1.72-1.84 (m, 2H), 1.84-1.96 (m, 2H), 1.98-2.09 (m, 2H), 5.40 (s, 1H), 7.11 (s, 1H), 8.02 (s, 1H).

Provenance & Evidence