Water → 5-(3-(((Tert-butyldiphenylsilyl)oxy)methyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of titanium (IV) chloride (9.88 g) in THF (80 mL) were added dropwise a solution of meldrum's acid (3.75 g) and 3-(((tert-butyldiphenylsilyl)oxy)methyl)benzaldehyde (6.50 g) in THF (50 mL) at 0° C., and pyridine (11.0 g) was further added dropwise at 0° C. over 30 min. The reaction mixture was stirred at 0° C. for 50 min, and water (100 mL) was added dropwise at 0° C. over 5 min. Water was further added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.40 g) as a white amorphous solid.

Provenance & Evidence