2-(Dimethylamino)ethanol → 2-Dimethylaminoethyl isobutyrate

Participants

Reaction Steps

To a mechanically stirred solution of 83.66 g (94.3 mL, 0.939 mol) of 2-dimethylaminoethanol (distilled) and 95 g (131 mL) of triethylamine (Aldrich gold label) in 1L of dry dichloromethane maintained at 0° to -15° C. was added dropwise 100 g (98.3 mL, 0.939 mol) of isobutyryl chloride. The mixture was stirred 30 min at room temperature and treated with a solution of 100 g of sodium bicarbonate in water. The organic layer was washed with dilute sodium bicarbonate solution, dried with sodium sulfate and distilled to give 46.2 g of 2-dimethylaminoethyl isobutyrate, b.p. 59°-64° C. (8-10 mm). 1H-NMR (360 MHz, benzene-d6): 1.06 (d, J=6.6 Hz, 6 H, Me2CH), 2.05 (s, 6 H, CH3N), 2.33 (t, J=6 Hz, 2 H, CH2N), 2.39 (sept, J= 6.6 Hz, 1 H, Me2CH), 4.11 (t, J=6 Hz, 2 H, CH2O). Anal Calcd for C8H17NO2 : C 60.35, H 10.76, N 8.80; found: C 60.82, H 10.95, N 9.01.

Provenance & Evidence