Sodium Chloride → HCID 10307904, compound

Participants

Reaction Steps

The general procedure A was applied to 4-methoxyacetophenone on a 112 mg (0.73 mmol) scale, using 10 mol % of Compound B (40 mg). The crude product was purified by column chromatography on silica gel (hexanes/EtOAc: 8/2) to give 3 (112 mg, 85.2% yield, 94.0% ee) as an oil: [α]D 20=−13.32 (c 1.8, CHCl3); 1H NMR (CDCl3, 500 MHz) δ 0.77 (dd, J=7.4, 7.4 Hz, 3H), 1.50 (s, 3H), 1.76-1.82 (m, 2H), 3.78 (s, 3H), 6.83-6.86 (m, 2H), 7.31-7.34 (m, 2H) ppm; 13C{1H} NMR (CDCl3, 125 MHz) δ 8.8, 29.9, 37.1, 55.6, 75.0, 113.7, 126.5, 140.3, 158.5 ppm; IR (NaCl) 3444, 2967, 1610, 1300, 1179 cm−1; MS (m/z relative intensity) 180 (M)+ (7), 165 (MCH3)+ (5), 163 (—OH)+ (49), 162 (M-H2O) (15); HMRS calcd for C11H15(—OH)+: 163.1122, found 163.1129.

Provenance & Evidence