Ethyl Acetate → 3-Methyl-4-pyridinecarboxaldehyde

Participants

Reaction Steps

1M Lithium aluminium hydride in tetrahydrofuran (6.96 ml, 6.96 mmol) in anhydrous tetrahydrofaran (15 ml) under a nitrogen atmosphere, was cooled to -10° C. and treated with ethyl acetate (0.61 g, 6.96 mmol) dropwise. After 10 minutes this solution was treated with dropwise addition of 3,N-dimethyl-N-phenyl-isonicotinamide (1.50 g, 6.63 mmol, J. Chem. Res., Synop. 1986, 20-21) in tetrahydrofuran (15 ml). After 2 hours at -10° C. the mixture was allowed to warm to room temperature. Methanol (10 ml) was added, followed by a saturated solution of potassium tartrate. The organic layer was separated and the aqueous layer was exhaustively extracted with dichloromethane. The combined organics were washed with water (2×10 ml), dried (sodium sulphate) then evaporated. The residue was purified by chromatography on silica using dichloromethane/methanol (40:1) to afford the aldehyde (560 mg, 70%) as a gum. MS, ES+, m/z=122 for (M+H)+, δH (360 MHz, DMSO-d6) 2.59 (3H, s), 7.68 (1H, d, J=5 Hz), 8.66 (1H, s), 8.70 (1H, d, J=5 Hz), 10-30 (1H, s).

Provenance & Evidence