Sodium Sulfite → (2R)-1-(3-Chlorophenyl)-2-hydroxypropan-1-one

Participants

Reaction Conditions

Reaction Steps

Z-1-(3-Chlorophenyl-tert-butyldimethylsilyloxy-1-propene (12.0 g, 44 mmol) was added to a well-stirred mixture of AD-mix-P (80 g) and CH3SO2NH2 (4.2 g, 44 mmol) in tert-butyl alcohol/water mixture (220 mL/220 mL) maintained at 0° C. The reaction mixture was stirred at 0° C. for 28 hours. Solid sodium sulfite (40 g) was added. The mixture was stirred for an additional 45 minutes and extracted with CH2Cl2 (2×100 mL). The combined organic extracts were washed with NaHCO3 and brine, and evaporated. The residue was passed through a silica gel column to give the desired product (7.0 g). 1H NMR (CDCl3): δ 1.45 (d, 3H), 5.15 (q, 1H), 7.2-7.9 (m, 4H).

Provenance & Evidence