Methanol → HCID 57540555, compound

Participants

Reaction Steps

To a solution of 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanone Part B (1.7 g, 5.96 mmol) in THF (12 mL) and MeOH (12 mL) was slowly added sodium borohydride (0.226 g, 5.96 mmol). After stirring at RT for 30 min, the mixture was concentrated, diluted with EtOAc, washed with sat NaHCO3, 1N HCl, brine, dried (Na2SO4) and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4-bromo-2-methoxyphenoxy)-1-cyclopropylethanol 16C (1.53 g, 5.33 mmol, 89% yield) as a clear oil. 1H NMR (400 MHz, chloroform-d) δ 6.97-7.07 (2H, m), 6.81 (1H, d, J=8.53 Hz), 4.14 (1H, dd, J=9.79, 2.76 Hz), 3.90-3.98 (1H, m), 3.85 (3H, s), 3.31 (1H, t, J=2.51 Hz), 2.78 (1H, s), 0.88-1.01 (1H, m), 0.49-0.67 (2H, m), 0.44 (1H, dd, J=9.41, 4.64 Hz), 0.25-0.33 (1H, m).

Provenance & Evidence