tert-Butanol → HCID 86684754, compound

Participants

Reaction Steps

AD-mix-beta (45 g) was added portion wise to a solution of 2 (4.5 g, 26.2 mmol) in t-butanol (135 mL) and H2O (135 mL) at 5° C. The mixture was stirred at room temperature for 16 hrs, and then cooled to 5° C. and treated with excess sodium sulfite for 20 min. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate, concentrated, and chromatographed on silica gel eluted with 67% ethyl acetate in hexanes and ethyl acetate to afford 5.0 g (92%) of 3 as a colorless oil. 1HNMR (CDCl3) δ 2.04 (2 H, brs), 2.81 (2 H, m), 3.54 (1 H, t, J=5.0 Hz), 3.75 (1 H d, J=11.0 Hz), 3.94 (1 H, m), 7.46 (1 H, d, J=9.0 Hz), 8.10 (1 H, s); LC/MS (M+1) 207.

Provenance & Evidence