tert-Butanol → HCID 131728321, compound

Participants

Reaction Steps

A mixture of Example 2 (4.7 g, 12.0 mmol), diphenylphosphoryl azide (3.63 g, 13 mmol) and triethylamine (1.31 g, 13 mmol) in 2-methyl-2-propanol (100 ml) was heated at 90° C. for 3 h. The reaction was cooled to r.t. and NaHCO3(aq) (200 ml) added. The mixture was extracted with DCM (3×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography (silica, 10% EtOAc in DCM) to give the title compound as a yellow solid (5.4 g, 90%). δH (CDCl3) 10.6 (1H, s), 7.62-7.46 (3H, m), 7.40-7.29 (6H, m), 6.81 (1H, d, J 9.7 Hz), 6.36 (1H, d, J 9.7 Hz), 2.37 (3H, s), 1.42 (9H, s). LCMS (ES+) RT 4.44 minutes, 461 (M+H)+.

Provenance & Evidence