Sodium Carbonate → 4-(5-Ethylpyrimidin-2-yl)benzaldehyde

Participants

Reaction Steps

A suspension of saturated aq. Na2CO3 (10 mL) and 4-formylphenylboronic acid (1.80 g, 12.0 mmol) in ethanol (5 mL) was added to a solution of 2-chloro-5-ethylpyrimidine (1.20 mL, 10.0 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.300 g, 0.5 mmol) in toluene (20 mL). The reaction mixture was heated to reflux for 5 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 3:1 hexanes/ethyl acetate) gave 1.62 g (76%) of the title compound. MS 213 (M+H)+.

Provenance & Evidence