Water → HCID 22748558, compound

Participants

Reaction Steps

Methyl 4-methoxy-trans-crotonate (6.5 g, 50 m.mole) and N-bromoacetamide (7.6 g, 55 m.mole) were dissolved together in peroxide-free dioxane (30 ml) and water (12 ml) was added. The solution was kept at room temperature in the dark for 7 days. The resulting clear, colourless solution was diluted with ether (150 ml) and washed three times with water (50 ml portions). The solution was dried (MgSO4) and the solvent removed under reduced pressure to yield a colourless oil (9.47 g) which was chromatographed on silica-gel (elution with ethyl acetate/petroleum ether) to give the erythro bromohydrin (e2) as a colourless oil (3.46 g, 30.5%).

Provenance & Evidence