Hydrochloric Acid → 2-methyl-6-phenyl-1H-pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2,6,6-tetramethylpiperidine (18.2 ml) in THF (160 ml) at −78° C. was added dropwise n-BuLi (43 ml, 2.5M solution in Hex). After the addition, the reaction mixture was stirred for 30 min at −78° C. To this solution was added intermediate 1.1 (6.17 g) in THF (20 ml) at −78° C. After addition, stirring was continued for 30 min. A solution of benzonitrile (4.67 ml) in THF (20 ml) at −78° C. was added dropwise. After addition, the mixture was slowly warmed to −50° C. and stirred for 20 min. The solution was poured into 10% aq. HCl (200 ml), stirred for 45 min at RT and neutralized with aq. NaOH to pH 9-10. The org. phase was separated, the aq. phase extracted twice with EA, and the combined org. phases dried over MgSO4. CC (Hept/EA 1:1, then DCM/MeOH 95:5, then DCM/MeOH 8:2) afforded 1.96 g of the desired compound.

Provenance & Evidence