Tetrahydro-4H-pyran-4-one → HCID 90414228, compound

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Reaction Steps

To a solution of Example 87A (200 mg, 0.504 mmol) in tetrahydrofuran (5 mL) at −78° C. was added 1.6M n-butyllithium in hexanes (0.473 mL, 0.757 mmol) under nitrogen. The mixture was stirred for 5 minutes and dihydro-2H-pyran-4(3H)-one (101 mg, 1.009 mmol) was added. Stirring was continued at −78° C. for 1 hour and the mixture was warmed to room temperature overnight. The mixture was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered and purified by flash chromatography (silica gel, 20-100% ethyl acetate/heptanes to afford the title compound. MS (ESI+) m/z 497.0 (M+H)+.

Provenance & Evidence