反应详情

温度

50 °C

To a solution of 1-propynyl magnesium bromide in THF (0.5 N, 322 mL, 161.28 mmol) is added a solution of 5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (20 g, 80.64 mmol) in THF (200 mL) by cannula under a nitrogen atmosphere. Over the course of the addition, the reaction mixture changed to a thick, yellow suspension. After addition is compete, the reaction mixture is stirred for 15 minutes at 50° C., quenched with aqueous NH4Cl, and acidified to pH ˜2 with 2 N HCl. The mixture is extracted with EtOAc (2×300 mL) and the combined extracts are washed with saturated brine, dried over MgSO4, filtered, and concentrated to a yellow solid (20 g, 86%). The product is carried on crude.

1. additionOver the course of the addition
2. additionAfter addition
3. customquenched with aqueous NH4Cl
4. extractionThe mixture is extracted with EtOAc (2×300 mL)
5. washthe combined extracts are washed with saturated brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated to a yellow solid (20 g, 86%)