Trifluoroacetic anhydride → (4-Methylpyridin-2-yl)methanol

A mixture of 2,4-dimethylpyridine N-oxide (10.9 g, 88.5 mmol) and trifluoroacetic anhydride (31 mL, 219 mmol) in dichloromethane (75 mL) was stirred at room temp. overnight. The product mixture was concentrated under vacuum. The residue was dissolved in a mixture of dichloromethane (75 mL) and aqueous sodium carbonate (225 mL, 2M), and stirred vigorously for 4 h. The resultant mixture was diluted with dichloromethane. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1-2% methanol in chloroform gradient. Collection and concentration of appropriate fractions provided 2-hydroxymethyl-4-methylpyridine as clear oil.

1. concentrationThe product mixture was concentrated under vacuum
2. dissolutionThe residue was dissolved in a mixture of dichloromethane (75 mL) and aqueous sodium carbonate (225 mL, 2M)
3. stirringstirred vigorously for 4 h
4. additionThe resultant mixture was diluted with dichloromethane
5. extractionThe organic extract
6. washwas washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customCollection and concentration of appropriate fractions

ORD record

ord-dc555756eb054cb6a19efc7c9065d6bc

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05891889