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

Participants

Reaction Steps

To a solution of 21.1 (8.00 g, 32 mmol) in THF (100 mL) was added a 2.0 M solution of cyclopropylmagnesium chloride in THF (97 mL, 193 mmol (commercially available from Aldrich)) dropwise at 0° C. over 1 hour. Upon completion of the addition, the mixture was quenched with 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was chromatographed on silica gel (20-30% EtOAc/hexane) to afford 21.2.

Provenance & Evidence