HCID 13015380, compound → HCID 13015381, compound

Participants

Reaction Steps

A solution of 4,5-bis(p-methoxyphenyl)-2-thiazoleacetic acid, methyl ester (2.5 g.; 0.0068 mole) and THF (10 ml.) was added dropwise by syringe to an ice cooled slurry of lithium aluminum hydride (0.55 g.; 0.0145 mole) and THF (20 ml.). Stirring was continued for an additional 1.25 hours at ambient temperature. The reaction was quenched by the dropwise addition of water (2 ml. via syringe) and then concentrated by rotary evaporation. The residue was slurried with water, taken to pH 4 with 6 N sulfuric acid, and extracted with methylene chloride. The extracts were washed with water, dried (sodium sulfate), and concentrated by rotary evaporation. The crude mixture was chromatographed (HPLC) with 50% ethyl acetate in benzene through silica gel and then recrystallized from ether-pentane to afford 0.82 g. (35% yield) 4,5-bis(4-methoxyphenyl)-2-thiazole ethanol; m.p. 101°-104° C.

Provenance & Evidence