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-225c87e4b9234500abbf9627801447ba

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343973B2