Sodium borohydride → HCID 15592688, compound

Participants

Reaction Steps

To a solution of 10.0 g (0.0375 mol) of the 2,2,2-trifluoro-1-(6-phenoxy-2-pyridinyl)ethanone of Step B in 100 ml of ethanol at 0° C. was added 1.5 g (0.0395 mol) of sodium borohydride portionwise over 5 to 10 minutes. The reaction was then warmed to room temperature and stirred overnight. After this time, the reaction was quenched with 1N aqueous HCl, neutralized with aqueous NaHCO3 and extracted with chloroform. The chloroform extracts were dried over MgSO4, filtered and concentrated to afford a yellow oil which solidified on standing to a waxy solid. Recrystallization from 4:1 hexane-ether afforded 6.13 g (60%) of the title compound as a white powder: m.p. 75° to 77° C.; 1H NMR (CDCl3) δ 4.67 (d, 1H), 4.92 (dq, 1H), 6.9-7.5 (m, 7H), 7.78 (t, 1H); IR (Nujol) 1570, 1600, 3390 cm-1.

Provenance & Evidence