Ammonium Chloride → (2,3,6-Trifluoropyridin-4-yl)methanol

To a stirred solution of benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester (3.43 g, 12.8 mmol) in anhydrous methanol (50 ml) at room temperature, was added sodium methoxide (693 mg, 12.8 mmol). After stirring for 20 min., excess ammonium chloride was added to the reaction mixture and stirring was continued for 30 min. The mixture was then evaporated in vacuo and the residue was dissolved in methanol-dichloromethane (1:9), filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:4) to EA) to afford 2.0 g (95%) of (2,3,6-trifluoro-pyridin-4-yl)-methanol as a white solid. m.p. 48-49° C.; 1H NMR (200 MHz, CDCl3) δ 2.18 (1H, t, J=5.6 Hz), 4.88 (2H, d, J=5.6 Hz), 7.02 (1H, s).

1. stirringstirring
2. waitwas continued for 30 min
3. customThe mixture was then evaporated in vacuo
4. dissolutionthe residue was dissolved in methanol-dichloromethane (1:9)
5. filtrationfiltered
6. customthe filtrate was evaporated in vacuo
7. customThe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:4) to EA)

ORD-Eintrag

ord-8486a0e3c9164bed8c604a90d8e44457

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08106064B2