methyl 6-(trifluoromethyl)nicotinate → 6-(Trifluoromethyl)pyridine-3-methanol

Participants

Reaction Steps

To a solution of Example 85A (4.1 g, 20.0 mmol) in 100 mL of methanol was added 7.6 g of NaBH4 in portions at 0° C. The resulting mixture was stirred at room temperature overnight, then quenched with water (100 mL). Most of the methanol was removed in vacuo. The residue was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column (petroleum ether:ethyl acetate=5:1) to afford the title compound (2.8 g, 79.1%). 1H NMR (400 MHz, CDCl3): δ 8.68 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.70 (s, J=8.0 Hz, 1H), 4.84 (s, 2H), 2.48 (s, br, 1H).

Provenance & Evidence