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

Participants

Reaction Steps

To a solution of 8.1 (8.00 g, 32 mmol) in THF (100 mL) was added allylmagnesium chloride (available from Aldrich) (2.0 M in THF) (97 mL, 193 mmol) dropwise at 0° C. over 1 hour. When the addition was complete, the reaction was quenched with 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (20-30% EtOAc/hexane) to afford 43.1 (3.4 g, 36%) as a pale yellow oil.

Provenance & Evidence