Water → HCID 70980750, compound

Participants

Reaction Conditions

Reaction Steps

5-[4-(Azidomethyl)phenyl]-1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole (162 mg, 0.435 mmol) and triphenylphosphine (342 mg, 1.30 mmol, 3 equiv) were combined in tetrahydrofuran (10 mL) at ambient temperature. After stirring for 5 minutes, the mixture was placed into a preheated oil bath at 50° C. for 2 hours. The mixture was treated with sodium bicarbonate (1.5 mL, aqueous saturated) and heated for an additional 1 hour at 50° C. The mixture was cooled to ambient temperature, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (25 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol containing 10% ammonium hydroxide), providing the titled compound as a light green gum.

Provenance & Evidence