Triethylamine → HCID 21903111, compound

Participants

Reaction Steps

N-hydroxysuccinimide (32.06 g) was suspended in ethyl acetate (150 ml). Propionic anhydride (37 ml) and triethylamine (39 ml) were added alternately in small portions. A solution formed and the vessel became warm as the reaction progressed. After cooling to room temperature, several milliliters of saturated saline were added, resulting in the precipitation of a thick crystalline mass (triethylammonium propionate). The solid was filtered and washed with ethyl acetate. The combined filtrate was washed with saturated saline (3×) and water (1×). Evaporation of the organic layer left a residue of oil, which crystallized upon scratching with a glass rod and trituration with petroleum ether to give 45.36 g of product (95.2% yield). Mp. 44°-46° C., analysis (C7H9NO4); calc. 49.62% C, 5.30% H, 8.18% N; found 49.29% C, 5.20% H, 8.19% N.

Provenance & Evidence