Hydrochloric Acid → HCID 22009803, compound

Participants

Reaction Steps

A mixture of 4-[2-[(E)-2-phenylethenyl]-4-oxazolyl methoxy]benzaldehyde (5.00 g), sodium borohydride (620 mg), tetrahydrofuran (50 ml) and ethanol (50 ml) was stirred for 16 hours at room temperature. The reaction mixture was poured into water and acidified with 2N hydrochloric acid. The resulting precipitate was collected by filtration and dried, which was suspended in chloroform (50 ml). To the suspension was added thionyl chloride (2.00 g). The mixture was stirred for one hour at room temperature. The reaction mixture was concentrated, to which was added ethyl acetate, followed by washing with saturated aqueous sodium hydrogencarbonate and water. The ethyl acetate layer was separated and dried (MgSO4). The solvent was distilled off to leave crystals, followed by recrystallization from chloroform-isopropyl ether to give 4-(4-chloromethylphenoxymethyl)-2-[(E)-2-phenylethenyl]oxazole (3.25 g, 61%) as colorless prisms, mp 116-117° C.

Provenance & Evidence