Water → HCID 69292149, compound

Participants

Reaction Steps

A solution of 4-fluorobenzaldehyde (5.86 g, 45 mmol) in dry THF (10 ml) was dropwise added at −70° C. to a solution of 2-fluoro-3-lithiopyridine (prepared from 2-fluoropyridine (3.91 ml, 45 mmol) and LDA (49.5 mmol)) in THF (120 ml). After complete addition, the cooling bath was removed and the reaction was allowed to reach 10° C. Hydrolysis was performed by addition of water, and the mixture is then diluted with ether. After separation of the layers, the ether solution was washed with brine, dried over Na2SO4 and evaporated in vacuum to yield a viscous oil. The alcohol was dissolved in CHCl3 (150 ml) and MnO2 (58.62 g, 0.675 mol) was added at room temperature. After 16 hours, the mixture was filtered on a pad of Celite and concentrated. The residual oil was chromatographied on silica gel (CH2Cl2) and (4-fluorophenyl)(2-fluoro-3-pyridinyl)methanone 37 was isolated as a white solid (4.83 g, 49%).

Provenance & Evidence