Ethyl Acetate → HCID 59698762, compound

Participants

Reaction Steps

A solution of 5,6-dichloro-pyridin-3-yl-methanol (10.0 g, 56.2 mmol), phenylboronic acid (7.5 g, 61.5 mmol), K2CO3 (20.0 g, 145 mmol) in H2O (140 mL) and dimethoxyethane (140 mL, 0.4 M), is degassed and treated with tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) and warmed to a gentle reflux under nitrogen for 4 h. After cooling to room temperature, ethyl acetate (100 mL) is added and the solids are filtered and washed with ethyl acetate (20 ml). The filtrate is extracted with ethyl acetate (100 mL) and the organic layer is washed with H2O (200 mL), saturated aq NaCl (200 mL) and dried over Na2SO4. The product is purified by MPLC (30-90% ethyl acetate in n-heptane) to provide 5-chloro-6-phenyl-pyridin-3-yl-methanol as a light yellow solid (12.0 g, 97%): Rf 0.24 (30% ethyl acetate in n-heptane), 1H NMR (CDCl3, 300 MHz) δ 8.47 (br s, 1 H), 7.78 (br s, 1 H), 7.70-7.65 (m, 2 H), 7.50-7.40 (m, 3 H), 4.67 (s, 2 H); ESI-LCMS m/z calcd for C12H10ClNO: 219.0; found 220.0 (M+1)+.

Provenance & Evidence