tert-Butanol → HCID 22053388, compound

Participants

Reaction Steps

A mixture of 19 (4.82 g, 22.1 mmol), DPPA (6.99 g, 25.4 mmol) and Et3N (3.69 mL, 26.5 mmol) in anhydrous t-BuOH (60 mL) was heated at reflux under N2 for 8 h. The mixture was concentrated under reduced pressure, and the residue was partitioned between CH2Cl2 and 10% aqueous KHCO3. The organic phase was washed with 10% aqueous KHCO3, dried (Na2SO4) and concentrated under reduced pressure, then chromatographed on silica gel. Elution with CH2Cl2/EtOAc (17:3), followed by sequential crystallisation from MeOH/H2O and CH2Cl2/petroleum ether gave 20 (3.82 g, 60%): mp 134–135° C.; 1H NMR [(CD3)2SO]δ 10.09 (s, 1 H), 8.87 (dd, J=4.1, 1.5 Hz, 1 H), 8.47 (dd, J=8.5, 1.6 Hz, 1 H), 8.33 (d, J=1.9 Hz, 1 H), 8.25 (d, J=2.2 Hz, 1 H), 7.65 ,m(dd, J=2.2 Hz, 1 H), 7.65 (dd, J=8.5, 4.2 Hz, 1 H), 1.53 (s, 9 H). Anal. Calcd. for C14H15N3O4: C, 58.12; H, 5.23; N, 14.53. Found: C, 58.39; H, 5.21; N, 14.65%.

Provenance & Evidence