tert-Butanol → HCID 60167284, compound

Participants

Reaction Conditions

Reaction Steps

Carboxylic acid 9 (950 mg, 2.66 mmol) was dissolved in freshly distilled t-BuOH (0.01 M) over 4 Å molecular sieves. Et3N (467 μL, 3.35 mmol) and diphenylphosphoryl azide (602 μL, 2.79 mmol) were added. The reaction mixture was warmed to 85° C. under Ar and stirred for 14 h. Upon completion, the mixture was filtered through cotton to remove the molecular sieves and concentrated under reduced pressure. The residue was diluted with 10% aqueous HCl and extracted with EtOAc (3×). The organic extracts were combined and washed with H2O (2×) and saturated aqueous NaCl. The organic phase was dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography (SiO2, 5×12 cm, 5% EtOAc/hexanes elution) provided 10 (1.02 g, 89%) as a tan solid. 1H NMR (CDCl3, 600 MHz) δ 7.62 (m, 2H), 7.58 (d, J=7.8 Hz, 2H), 7.49 (s, 1H), 7.39 (t, J=7.2 Hz, 2H), 7.33 (t, J=6.0 Hz, 1H), 7.16 (t, J=7.8 Hz, 1H), 7.03 (s, 1H), 6.58 (s, 1H), 5.22 (s, 2H), 1.54 (s, 9H). 13C NMR (CDCl3, 150 MHz) δ 155.2, 152.5, 137.6, 136.4, 136.3, 131.3, 130.0, 128.4, 127.9, 127.3, 126.9, 120.4, 120.2, 120.1, 116.6, 107.8, 101.8, 71.4, 28.3. IR (film) νmax 3325, 2977, 1702, 1156 cm−1. ESI-TOF HRMS m/z 428.0856 (M+H+, C22H22BrNO3 requires 428.0856).

Provenance & Evidence