Pyridine → HCID 19699952, compound

Participants

Reaction Steps

20 ml of acetic anhydride was dropwise added to a comprising 22.8 g of the 2-[4-[α-hydroxy-4-(1-methoxymethyloxyethyl)benzyl]phenyl]-1,3-dioxolane prepared in the step (a) and 30 ml of pyridine, and the obtained mixture was stirred at room temperature for 3 hours. After the completion of the reaction, 10 ml of water was added to the reaction mixture and the obtained mixture was further stirred for 30 minutes and poured onto ice-water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with 1N hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt successively, dried and distilled to remove the solvent, giving a colorless oil. 2 ml of pyridine, 100 ml of ethanol and 3 g of palladium/carbon were added to the oil and the obtained mixture was stirred in a hydrogen atmosphere at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was filtered and the filtrate was subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography [hexane/ethyl acetate (85:15)] to give 21 g of the title compound.

Provenance & Evidence