Acetone → HCID 67270159, compound

To a stirred suspension of 6-methylpyridin-3-ol (2.54 g, 23.3 mmol) in tetrahydrofuran (100 mL) was added n-butyllithium solution (1.6 M in n-hexane, 32 mL, 51.2 mmol) dropwise at −20° C. After addition, the mixture was allowed to warm to room temperature and stirred at the same temperature for 1 h. Then the mixture was cooled to −78° C., and acetone (2.03 g, 35.0 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature over 20 h. The mixture was quenched with acetic acid (5.8 mL) and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with acetone/n-hexane (1:1) to give 3.90 g (quant.) of the title compound as a yellow oil.

1. additionAfter addition
2. temperatureThen the mixture was cooled to −78° C.
3. temperatureto warm to room temperature over 20 h
4. customThe mixture was quenched with acetic acid (5.8 mL)
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was chromatographed on a column of silica gel eluting with acetone/n-hexane (1:1)

ORD record

ord-3c9af78b9a714e82bfc60294216b6c31

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906532B2