tert-Butanol → HCID 44549669, compound

Participants

Reaction Steps

A solution of acid 169 (550 mg, 2.57 mmol), DPPA (850 mg, 3.08 mmol) and Et3N (570 mg, 5.65 mmol) in t-BuOH (20 mL) was heated under reflux for 15 h. The mixture was poured into EtOAc and filtered through Celite. Chromatography on silica gel eluting with petroleum ether/CH2Cl2/EtOAc (8:1:1) gave tert-butyl 7-acetyl-2-naphthylcarbamate (170) (451 mg, 62%) as a colorless solid: mp (EtOAc) 161-163° C.; 1H NMR (CDCl3) δ 8.38 (br s, 1H), 8.16 (br s, 1H), 7.91 (dd, J=8.5, 1.7 Hz, 1H), 7.80 (d, J=8.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.43 (dd, J=8.8, 2.2 Hz, 1H), 6.68 (br s, 1H), 2.70 (s, 3H), 1.55 (s, 9H); 13C NMR δ 198.2, 152.7, 136.7, 135.0, 133.2, 132.0, 1297, 128.5, 128.0, 122.4, 121.6, 115.8, 81.0, 28.3, 26.6. Anal. (C17H19NO3) C, H, N.

Provenance & Evidence