Methyl 6-methoxypyridine-3-carboxylate → (6-Methoxypyridin-3-yl)methanol

Temperature

100 °C

A solution of methyl 2-methoxypyridine-5-carboxylate (8.4 g, 50 mmol) in dixoane (70 mL) was treated with sodium borohydride (8.1 g, 244 mmol) at 0° C. The reaction mixture was warmed to 100° C. and heating continued overnight. After this time, the mixture was cooled, diluted with methanol, filtered through a fritted funnel with methanol washes, and the filtrate was concentrated. The residue was redissolved in water, 0.5 M sodium hydroxide was added dropwise, and the mixture extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (2.9 g, 35%) as a colorless oil. MW=139.15. 1H NMR (CD3OD; 300 MHz) δ 8.11-8.05 (m, 1H), 7.67 (dd, J1=10.9 Hz, J2=2.43 Hz, 1H), 6.77 (d, J=8.5 Hz, 1H), 4.89 (s, 1H), 4.54 (s, 2H), 3.89 (s, 3H); APCI MS m/z 140 [M+H]+.

1. temperatureheating
2. temperatureAfter this time, the mixture was cooled
3. filtrationfiltered through a fritted funnel with methanol washes
4. concentrationthe filtrate was concentrated
5. dissolutionThe residue was redissolved in water
6. addition0.5 M sodium hydroxide was added dropwise
7. extractionthe mixture extracted with ethyl acetate
8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

ORD record

ord-0da34e4ef1d447b8844587c3e9abc157

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2