Water → Carbamic acid, N-[2-(3-methoxyphenyl)ethyl]-, ethyl ester

Participants

Reaction Steps

To an ice-cold solution of 2-(3-methoxyphenyl)-1-ethanamine (5.00 g, 33.1 mmol) and Et3N (5.10 mL, 3.70 g, 36.6 mmol) in CH2Cl2 (100 mL) was added ethyl chloroformate (3.50 mL, 3.62 g, 33.4 mmol). The resulting solution was allowed to warm to RT and was stirred for 2 h. Water (100 mL) was added and the mixture was extracted with CH2Cl2 (3×50 mL), dried (MgSO4) and concentrated to yield ethyl 3-methoxyphenethylcarbamate (7.32 g, 99% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.22 (t, J=7.8 Hz, 1H), 6.78 (d, J=8.0 Hz, 1H), 6.77 (d, J=8.0 Hz; 1H), 6.74 (s, 1H), 4.65 (brs, 1H), 4.11 (q, J=7.2 Hz, 2H), 3.80 (s, 3H), 3.44 (q, J=6.4 Hz, 2H), 2.79 (t, J=7.0 Hz, 2H), 1.23 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 224.2 (M+H+).

Provenance & Evidence