5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-(1-(3-Hydroxyphenyl)-2-propenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Participants

Reaction Steps

To a solution of 8.1 (6.0 g, 24.17 mmol) in THF, was added vinylmagnesium bromide (available from Aldrich) (207.2 mL, 145.0 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 over Na2SO4, filtered, and concentrated to provide 15.1 as a yellow oil which was used in the next step without further purification.

Provenance & Evidence