Acetone → HCID 67270159, compound

Participants

Reaction Steps

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.

Provenance & Evidence