3-Nitrobenzaldehyde → HCID 67465982, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (methoxymethyl)triphenylphosphonium chloride (6.79 g 19.85 mmol) in anhydrous THF (50 mL) was cooled to −20° C. and potassium tert-butoxide (2.67 g. 23.82 mmol) was added in lots to give a red reaction mass. The mixture was cooled to −30° C. and a solution of 3-nitrobenzaldehyde (2.0 g, 12.12 mmol) in toluene (15 mL) was added gradually over 30 minutes. The mixture was stirred for 1 hour then EtOAc (2 mL) followed by saturated ammonium chloride were added at 0° C. The reaction mixture was extracted with EtOAc (2×75 mL). The combined organic extracts were washed with brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude compound was purified by column chromatography on neutral silica gel using DCM to afford the title compound (1.8 g, 76%) as a solid.

Provenance & Evidence