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

Participants

Reaction Steps

To a 0.5M tetrahydrofuran solution of 1-propynylmagnesium bromide (800 mL) was added dropwise a solution of 5-(4-hydroxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dion e (47.3 g) obtained in Substep 1 in tetrahydrofuran (650 mL) under argon atmosphere at 11° C. over 40 minutes, followed by stirring the reaction mixture at room temperature for 1 hour. Then, to the reaction mixture were added successively aqueous ammonium chloride solution (34 g/l L) and hexane (1 L), followed by removing the organic layer. After adding saturated aqueous potassium hydrogen sulfate solution to the aqueous layer and adjusting a pH to 1, the aqueous layer was extracted with ethyl acetate twice. The organic layer was dried and concentrated to give 5-[1-(4-hydroxyphenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxan e-4,6-dione (54.8 g).

Provenance & Evidence