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

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).

1. extractionIt was extracted with EtOAc (150 mL)
2. washwashed with water (6 mL×3) and brine (6 mL)
3. dry with materialThe extract was dried over MgSO4
4. customevaporated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel
6. washeluted with hexane/EtOAc 4:1

ORD record

ord-9ef8582ecb024ebe87fb7d104778ee74

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414036B2