5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

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Reaction Steps

To a solution of 8.1 (2.0 g, 8.06 mmol) in THF, was added cyclopropylmagnesium bromide (available from Aldrich) (96.7 mL, 48.3 mmol) via cannula at 0° C. The resulting heterogeneous mixture was warmed to room temperature, stirred for 30 minutes, and quenched with 1 N aq. HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel flash chromatography (10-35% EtOAc/hexane) to afford 8.2 (2.04 g, 87.2% yield) as a yellow oil.

Provenance & Evidence