Ethoxyacetic acid → N-benzyl-2-ethoxy-N-ethylacetamide

Participants

Reaction Steps

A suspension of 1,1′-carbonyldiimidazole (4.68 g, 28.86 mmol) in dry DCM (15 mL) was added portion-wise over 15 min to a solution of ethoxyacetic acid (2.09 mL, 22.12 mmol) in DCM (30 mL) under nitrogen at room temperature. The resulting solution was stirred under nitrogen for 1 h and then treated with a solution of N-ethylbenzylamine (6.60 mL, 44.37 mol) in dry dichloromethane (30 mL) drop-wise over 15 min. The resultant solution was stirred under nitrogen at room temperature for 18 h and then partitioned with aqueous HCl (2M, 2×75 mL) and the combined organic layer dried (MgSO4), filtered and reduced in vacuo to give an oil. Purification by SPE (silica, 2×50 g cartridges), eluting with cyclohexane:EtOAc gradient 15:1 to 1:1 afforded the title compound as a pale yellow oil (4.36 g).

Provenance & Evidence