Hydrochloric Acid → (6-Methylpyridin-3-yl)methanol

Temperature

-78 °C

5-Methoxycarbonyl-2-methyl-pyridine (3.0 g, 19.8 mmole) was dissolved in toluene (60 ml) and cooled to -78° C. To this solution, a 39.7 ml of a solution of 1M diisobutylaluminum hydride in toluene was added dropwise. The reaction mixture was stirred for 1 hour at -78° C., allowed to warm to room temperature and stirred for an additional 18 hours. Methanol (8 ml) was then added dropwise at room temperature to the reaction mixture. The mixture was stirred until a thick gel was formed. 1N HCl (10 ml) was added to dissolve the gel. The resulting phases were separated, the organic phase was extracted in ethyl acetate and dried over MgSO4. The solvents were removed yielding crude 5-hydroxymethyl-2-methylpyridine (540 mg) as an oil, which was used without further purification.

1. temperatureto warm to room temperature
2. stirringstirred for an additional 18 hours
3. stirringThe mixture was stirred until a thick gel
4. customwas formed
5. dissolutionto dissolve the gel
6. customThe resulting phases were separated
7. extractionthe organic phase was extracted in ethyl acetate
8. dry with materialdried over MgSO4
9. customThe solvents were removed

ORD record

ord-ef3f500433cb4cc3a0d9c6758f3fbccc

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05264437