Ammonium Chloride → 1-(6-Fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

(6-Fluoropyridin-3-yl)(4-(methylthio)phenyl)methanone (1.256 g, 5.079 mmol) was dissolved in THF (19 mL) and the flask was cooled in an ice water bath. Then, methylmagnesium bromide (3.0 M in diethyl ether, 3.40 mL, 10.2 mmol) was added via syringe over 5 min. The reaction was stirred at 0° C. under nitrogen for 20 min, and then was treated with saturated ammonium chloride (2.5 mL, added dropwise at first as gas evolution is observed). The reaction was quenched at 0° C. Then, the reaction was diluted with water (15 mL) and the layers were separated. The aqueous phase was extracted with DCM, and the organic phases were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum at room temperature overnight to give 1-(6-fluoropyridin-3-yl)-1-(4-(methylthio)phenyl)ethanol (1.375 g). 1H NMR (CDCl3, 400 MHz) δ 8.26 (d, J=2.35 Hz, 1H), 7.82-7.76 (m, 1H), 7.35-7.30 (m, 2H), 7.25-7.20 (m, 2H), 6.86 (dd, J=8.61 Hz, 2.93 Hz, 1H), 2.48 (s, 3H), 2.30 (s, 1H), 1.96 (s, 3H). m/z (ESI, +ve ion) 264 (M+H)+.

Provenance & Evidence