Water → HCID 462653, compound

Participants

Reaction Steps

To a stirred solution of the silyloxyazide 15 (100 mg; 0.31 mmol) in distilled THF (5 mL) was added at room temperature water (6.7 μL), followed by the sequential addition, in one portion, of triphenylphosphine (97 mg; 0.37 mmol) and triphosgene (460 mg; 1.55 mmol). The reaction mixture was shielded from light and stirred at room temperature overnight. The reaction mixture was chromatographed on silica gel, eluting with 10% ethyl acetate in hexane, to afford 27.4 mg (40.4%) of the title chloride 28. 1H NMR (CDCl3) δ6.425 (dd, J=6.4, 6.0 Hz, 2H, C=CH), 4.267 (s, 2H, CH2), 4.004 (s, 2H, CH2); 13C NMR (CDCl3) δ128.538, 28.417, 127.719, 127.582, 54.864, 46.634.

Provenance & Evidence