Sodium Hydroxide → N-(tert-butyl)-N-phenylformamide

Participants

Reaction Steps

A solution of 1a (1.2212 g, 8.18 mmol) and acetic formic anhydride (1.2 mL, 15 mmol) in THF (10 mL) was stirred for 7 h at room temperature. To the reaction solution was added an aqueous NaOH solution (1.0 M, 20 mL) The organic phase was extracted with Et2O (30 mL×2) and was chromatographed (4:1 hexanes/EtOAc) to give 2a (1:1 mixture of isomers, 1.076 g, 74.2%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.72 (s, 0.5H), 8.16 (s, 0.5H), 7.51-7.29 (m, 3H), 7.19-6.99 (m, 2H), 1.40 (s, 9H); 13C NMR (75 MHz, CDCl3): δ 163.4, 162.6, 141.0, 138.2, 130.3, 130.1, 129.3, 129.2, 128.4, 57.7, 56.7, 31.0, 29.2. HRMS-ESI (m/z): [M+H]+ calcd for C11H15NO, 178.1226. found: 178.1228.

Provenance & Evidence