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

Participants

Reaction Steps

To a solution of 5-(3-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6S (2.00 g, 8.06 mmol) in THF (25 mL) was added cyclopropylmagnesium bromide (available from Aldrich) (0.5M, 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 aqueous HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel flash chromatography (10-35% EtOAc/hexane) to afford 5-(cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6T (2.04 g, 87% yield) as a yellow oil.

Provenance & Evidence