Sodium borohydride → (6-Methoxypyridin-2-yl)methanol

Temperature

0 °C

Methyl-6-methoxypyridine-2-carboxylate (2 g, 11.96 mmol) in anhydrous methanol (20 mL) was cooled to 0° C. under nitrogen and sodium borohydride (1.36 g, 35.89 mmol) was slowly added to the solution. The reaction was left stirring at 0° C. for 30 minutes, then allowed to warm up to room temperature for 1 hour. The reaction was quenched with water and concentrated on the rotovap. The reaction was diluted with brine (100 mL) and extracted with dichloromethane/2-propanol solution (2:1) (3×, 150 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated on the rotovap to afford (6-methoxypyridin-2-yl)methanol (500 mg, 30%) as an oil. MS M+H calculated 140.1. Found 140.1.

1. waitThe reaction was left
2. temperatureto warm up to room temperature for 1 hour
3. customThe reaction was quenched with water
4. concentrationconcentrated on the rotovap
5. additionThe reaction was diluted with brine (100 mL)
6. extractionextracted with dichloromethane/2-propanol solution (2:1) (3×, 150 mL)
7. dry with materialThe combined organic extracts were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated on the rotovap

ORD record

ord-043de570b8b84937a63c6f9871c9127f

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09247759B2