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

Participants

Reaction Steps

To a 250 mL 3-necked RB flask fitted with magnetic stirrer was charged with bromo(prop-1-yn-1-yl)magnesium (42.5 mL, 211 mmol) in THF (30 mL). To the RM was added slowly 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (5.0 g, 100.8 mmol) in THF (20 mL) under nitrogen atmosphere. The RM was stirred at room temperature about 30 minutes. The reaction mixture was diluted with NH4Cl solution and hexane. The aqueous layer was acidified with KHSO4 solution to adjust the pH 2 and extracted with ethyl acetate, washed with water, then dried to obtain the product (5.8 g, yield: 100.0%).

Provenance & Evidence