Ethyl bromoacetate → Ethyl 3-oxo-4-morpholineacetate

Participants

Reaction Steps

A solution of 3-oxo-morpholine (6.5 g, 4 mmol) (Willey, Alan David; Kott, Kevin Lee; Miracle, Gregory Scot; Gosselink, Eugene Paul; Burckett-St. Laurent, James Charles Theophile Roger. Bleaching compositions containing bleach activators having alpha-modified lactam leaving-groups. PCT Int. Appl. (1996), WO 9622350 A1) in DMF (45 mL) was treated at rt in 3 portions with sodium hydride (3.34 g, 60% dispersion in mineral oil, 84 mmol). After 30 min a solution of ethyl bromoacetate (11.8 g, 71 mmol) in DMF (20 mL) was added dropwise. After 3 h the solvent was evaporated, the residue was taken up with ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, dichloromethane:methanol=1000:0 to 995:5). The title compound was obtained as a light yellow oil (3.34 g, 28%). 1H-NMR (300 MHz, DMSO): δ=1.19 (t, J=7 Hz, 3H), 3.40 (mc, 2H), 3.85 (mc, 2H), 4.05-4.28 (m, 6H)

Provenance & Evidence