1-(6-Chloropyridin-3-yl)ethan-1-one → 2-(6-Chloropyridin-3-yl)propan-2-ol

Participants

Reaction Steps

To a solution of 1-(6-chloropyridin-3-yl)ethanone (2.0 g, 12.85 mmol) in THF (Volume: 25 mL) was added methyllithium (16.07 mL, 25.7 mmol) at 0° C. The reaction was stirred for 1 hr and allowed to warm to room temperature. The resulting deep red solution was quenched with water (Volume: 50 mL), extracted with EtOAc (1×50 mL), and the organic layer was dried over MgSO4. The organic phase was filtered and the filtrate was evaporated to dryness via rotary evaporation. The resulting material was purified via MPLC (DCM:MeOH, 95:5) to provide 2-(6-chloropyridin-3-yl)propan-2-ol (0.985 g, 5.74 mmol, 44.6% yield) as a dark red solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (s, 5 H) 5.32 (s, 1 H) 7.44 (d, J=8.34 Hz, 1 H) 7.90 (dd, J=8.34, 2.53 Hz, 1 H) 8.49 (d, J=2.53 Hz, 1 H). ESI-MS:m/z 172.0 (M+H)+.

Provenance & Evidence