Water → (6-Methylpyridin-3-yl)methanol

A solution of methyl 6-methylnicotinate (30 g, 198 mmol) in dry THF (150 mL) was added dropwise into a suspension of LiAlH4 (11 g, 289 mmol) in THF (200 mL) at 0 to −5° C. The grey suspension was stirred at RT for 1 h. The reaction mixture was cooled to −5 to 0° C. and water (11 mL) was added dropwise under nitrogen followed by slow addition of 15% NaOH (11 mL) and water (33 mL). The reaction was warmed to RT and stirred for 30 min. at RT. The resulting suspension was filtered and the filtrate was concentrated under vacuum to give (6-methylpyridin-3-yl)methanol as a yellow oil (23 g).

1. temperatureThe reaction mixture was cooled to −5 to 0° C.
2. temperatureThe reaction was warmed to RT
3. stirringstirred for 30 min. at RT
4. filtrationThe resulting suspension was filtered
5. concentrationthe filtrate was concentrated under vacuum

ORD record

ord-63bfc51297a6405bbd8aed0e12507c45

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193728B2