Methyl 5-methylpicolinate → (5-Methylpyridin-2-yl)methanol

Sodium borohydride (4.5 g, 115. mmol) was added to a solution of methyl 5-methylpicolinate (6.0 g, 39.5 mmol) in THF (60 mL) and methanol (6 ml) at RT. The reaction mixture was stirred at RT for 2 h (the reaction was monitored by TLC). The mixture was concentrated under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The organic layer was concentrated under vacuo to afford (5-methylpyridin-2-yl)methanol (3.5 g, 72.9%,) as an off-white solid. 1H NMR: 200 MHz, CDCl3: δ 8.5 (s, 1H), 7.7 (d, 1H), 7.15 (d, 1H), 5.0 (s, 3H), 3.4 (s, 3H). MS: [M+H]+: m/z=124.0.

1. concentrationThe mixture was concentrated under reduced pressure
2. additionthe residue was diluted with water
3. extractionextracted with EtOAc
4. dry with materialThe combined organics were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. concentrationThe organic layer was concentrated under vacuo

ORD record

ord-aee4621584044d9f933ef8cdc7819a9c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946222B2