Sodium borohydride → (2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanone (1.0 g, 2.8 mmol) was dissolved in MeOH (15 mL) and cooled to 0° C. NaBH4 (318 mg, 8.4 mmol) was added. The reaction mixture was quenched by aq. NH4Cl (15 mL) and extracted with EtOAc (100, 30, and 20 mL). The combined extracts were washed with brine (15 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography (5:1, hexanes:EtOAc) to provide 3d (980 mg, 97%) as a white powder. 1H NMR (300 MHz, CDCl3): δ 7.69 (d, J=8.4 Hz, 1H), 7.38 (d, J=3.0 Hz, 1H), 7.31 (dd, J=8.2, 3.0 Hz, 1H), 6.91 (s, 2H), 6.61 (d, J=2.1 Hz, 1H), 3.85 (s, 3H); 13C NMR (75 MHz, CDCl3): δ 159.6, 137.8, 136.3, 133.9, 133.0, 130.5, 129.6, 129.6, 128.0, 126.6, 115.4, 115.4, 70.2, 55.9; IR (film): 3482 cm−1, 1438, 1410, 1325;

Provenance & Evidence