1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 1-(6-(Hydroxymethyl)pyridin-2-yl)ethanone

関与物質

反応手順

To a THF (10 mL) solution of the silyl ether 2-Acetyl-6-(((tert-butyldimethylsilyl)oxy)methyl)pyridine (0.8 g, 3.0 mmol) was added tetrabutylammonium fluoride hydrate (870 mg, 3.3 mmol) at room temperature, and the mixture was stirred for 40 min. It was extracted with EtOAc (150 mL) and washed with water (6 mL×3) and brine (6 mL). The extract was dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with hexane/EtOAc 4:1 to give the title compound (450 mg, 99%) as an oil. 1H NMR (CDCl3) δ 8.00 (d, 1H, J=7.2 Hz, H-3), 7.88 (m, 1H, H-4), 7.49 (d, 1H, J=7.7 Hz, H-5), 4.88 (d, 2H, J=5.0 Hz, CH2), 3.84 (d, 1H, J=3.2 Hz, OH), 2.78 (s, 3H, CH3); 13C NMR (CDCl3) δ 200.0 (CO), 159.1 (C-6), 152.7 (C-2), 138.0 (C-4), 124.4 (C-5), 120.8 (C-3), 64.3 (CH2), 26.3 (CH3).

情報源と証拠