Diethyl Ether → HCID 86751272, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromothiazole in 12 ml of ether at -78° C., 2.1 ml of 2.5M n-butyl lithium were added dropwise over 30 minutes. The resulting brown suspension was stirred at -78° C. for 2 hours and then a solution of 2-(trifluoromethyl) -benzaldehyde in 2 ml of diethyl ether was added dropwise. The reaction was quenched 1 hour later with 10 ml of water saturated with ammonium chloride. The reaction mixture was extracted twice with 2 ml of diethyl ether. The organic phases were combined, dried (MgSO4) and concentrated in vacuo to yield 1.16 g of a brown oil. This oil was heated to 50° C. at 0.01 mm Hg to remove volatiles leaving 1.16 g of brown oil which was then chromatographed on silica gel using hexane-ethyl acetate (75-25) as the eluant. She last fraction to come off the column contained 297 mg of the desired product, 5-(1-hydroxy-2'-trifluoromethylbenzyl)-thiazole.

Provenance & Evidence