p-Toluenesulfonic acid → HCID 57175086, compound

Participants

Reaction Steps

560 mg of 3-(dimethoxymethyl)benzyltriphenylphosphonium bromide synthesized by brominating 3-hydroxymethylbenzaldehyde with phosphorus tribromide, and then acetalizing the product in anhydrous methanol in the presence of p-toluenesulfonic acid, followed by reacting it with triphenylphosphine] and 180 mg of 3-(1-pyrrolyl)benzaldehyde [synthesized by oxidizing 3-(1-pyrrolyl)benzyl alcohol with pyridinium chlorochromate in chloroform]were dissolved in 20 ml of methanol. 110 mg of sodium methoxide was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was worked up in a customary manner, and purified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=10/1] to give 135 mg (yield 42%) of an E-form of 3-[2-[3-(1-pyrrolyl)phenyl]ethenyl]benzaldehyde dimethyl acetal and 127 mg of its Z-form.

Provenance & Evidence