tert-Butanol → HCID 45092150, compound

Participants

Reaction Steps

A solution of 321 mg (2.27 mmol) of 2-(3-methylisoxazol-5-yl)acetic acid, 0.5 mL (2.32 mmol) of diphenylphosphorylazide (DPPA), and 0.35 mL (2.51 mmol) of triethylamine in 30 mL of distilled tert-butyl alcohol was refluxed for 13.5 hours. The solution was concentrated, and the crude residue was dissolved in EtOAc. The organic layer was washed with 1N HCl (3×10 mL) and saturated NaHCO3 solution (3×10 mL). The organic layer was dried over sodium sulfate, filtered, concentrated. Purification by flash silica gel chromatography (28% EtOAc/hexanes) provided 50 mg (10% yield) of tert-butyl (3-methylisoxazol-5-yl)methylcarbamate as a pale yellow solid.

Provenance & Evidence