反应详情

A round bottomed flask was charged with a magnetic stir bar and methyl 2-(2-bromophenyl)acetate (25 g, 109 mmol) and THF (50 mL). This solution was cooled to −78° C. before drop wise addition of a 1M solution of LiHMDS in THF (218 ml, 218 mmol). The reaction was stirred for 30 min at −78° C. before addition of 1-(1H-imidazol-1-yl)ethanone (14.42 g, 131 mmol) dissolved in a mixture of THF:DMF (112 mL THF, 24 mL DMF). The solution was stirred for 1H before quenching with sat'd aqueous NH4Cl (˜250 mL) and diluting with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (˜2×250 mL). The combined organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography using an eluent of ethyl acetate/hexanes (10:1) to afford methyl 2-(2-bromophenyl)-3-oxobutanoate (32.5 g, 102 mmol, 93% yield).

1. additionA round bottomed flask was charged with a magnetic stir bar
2. custombefore quenching with sat'd aqueous NH4Cl (˜250 mL)
3. additiondiluting with EtOAc
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with EtOAc (˜2×250 mL)
6. extractionThe combined organic extract
7. washwas washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude residue was purified via silica gel chromatography