Acetic Acid → 3-(2-Methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (2.024 mL, 10.78 mmol) was added to a stirred solution of tetrahydro-4H-pyran-4-one (0.948 mL, 10.27 mmol) in toluene (3 mL) at 0° C. After 2 minutes 1-(1H-imidazol-1-yl)-2-methoxy-2-phenylethanone (1.110 g, 5.13 mmol) was added and the mixture was stirred at 0° C. for 5 minutes. The reaction was quenched with acetic acid (0.882 mL, 15.40 mmol) in 5 mL water. The organic layer was separated and concentrated. The crude product was purified by silica flash chromatography using ethyl acetate (0 to 40%) in heptane giving 3-(2-methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one (0.245 g, 19%). MS (ES−) m/z 247 (M−H)−

Provenance & Evidence