Phenacyl bromide → HCID 10870609, compound

Participants

Reaction Steps

To a stirring solution of ethyl 3-oxo-3-phenylpropanoate 67 (0.754 g, 3.92 mmol) in THF cooled to 0° C. was added potassium tert-butoxide (0.556 g, 4.71 mmol) and the reaction mixture was stirred for 10 minutes followed by the addition of 2-bromo-1-phenylethanone 68 (0.859 g, 4.32 mmol). The reaction mixture was allowed to stir at room temperature for 90 minutes then quenched with ethanol (2) and poured into ethyl acetate and layer separated. The organic layer was washed with water, brine, dried over Na2SO4, then purified by ISCO (40 g column, 0 to 35% ethyl acetate in hexane) to afford compound 69 (0.812 g, 67% yield) as a yellow oil. LRMS (ESI): (calc.) 310.12 (found) 311.08 (MH)+

Provenance & Evidence