Hydrochloric Acid → [4-(Pyrimidin-2-yl)phenyl]acetaldehyde

Participants

Reaction Conditions

Reaction Steps

Sodium hexamethyldisilazide (1.0M in THF, 2.65 mL, 2.65 mmol) was added to a suspension of methoxymethyltriphenylphosphonium chloride (0.93 g, 2.71 mmol) in THF (13 mL) at 0° C., and the red-orange mixture was stirred for 15 min at 0° C. A solution of 4-(2-pyrimidinyl)benzaldehyde (250 mg, 1.36 mmol, prepared as described in WO 9828264) in THF (5 mL) was added, and stirring was continued at 0° C. for 1 h. 10% aq. HCl (13 mL) was added and the mixture was heated to 50° C. for 1 h. The reaction mixture was then cooled to 0° C. and solid Na2CO3 was added cautiously until the solution was basic. The mixture was extracted with ethyl acetate (2×25 mL) and the combined organic extracts were washed with brine (2×25 mL), dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 2:1 hexane/ethyl acetate) yielded 141 mg (52%) of the title compound. MS 199 (M+H)+.

Provenance & Evidence