Hydrochloric Acid → HCID 53926632, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 0.53 g of sodium hydride (60% oil dispersion) was added to 20 ml of dry dimethylformamide, and 2.77 g of trimethylphosphonoacetate were added dropwise over 5 minutes with ice-cooling. After dropwise addition, stirring was continued at room temperature for 30 minutes. A solution of 2.02 g of 2-formyl-6-phenoxypyridine in 5 ml of dry dimethylformamide was added dropwise thereto over 5 minutes with ice-cooling. After dropwise addition, stirring was continued at room temperature for 14 hours. The reaction solution was poured into ice water, neutralized to a pH of 6.8 with aqueous dilute hydrochloric acid, and then extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure, and the residue was column-chromatographed on silica gel (developing solvent, n-hexane:ethyl acetate=7.1) to obtain 2.1 g of the desired methyl 3-(6-phenoxypyridin-2-yl)propenate.

Provenance & Evidence