Acetic Anhydride → (5-Methylpyridin-2-yl)methanol

2,5-Dimethylpyridine 1-oxide (2.5 g, 20.3 mmol) was added to acetic anhydride (8.2 mL) at 100° C. over a period of 30 min. Then the mixture was refluxed 1 h. The mixture was cooled to room temperature and carefully quenched with ethanol (11 mL). The reaction mixture was concentrated. The residue was treated with 1N HCl (6 mL) and refluxed 1 h. The reaction was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and concentrated to give (5-methylpyridin-2-yl)methanol (2 g, 80.0% yield) as a light yellow oil. LCMS MH+ 124.

1. temperatureThen the mixture was refluxed 1 h
2. customcarefully quenched with ethanol (11 mL)
3. concentrationThe reaction mixture was concentrated
4. additionThe residue was treated with 1N HCl (6 mL)
5. temperaturerefluxed 1 h
6. concentrationThe reaction was concentrated
7. customthe residue was partitioned between ethyl acetate and water
8. dry with materialThe organic phase was dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-88dbefc562724a138c7be69222a7800d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359359B2