Pyridine → HCID 57707106, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0M solution of titanium tetrachloride in DCM (9.3 mL, 9.3 mmol) was injected dropwise to THF (15 mL) cooled to 0° C. A solution of 1-(3-(benzyloxy)phenyl)ethanone (1.0 g, 4.42 mmol) (commercially available from Aldrich) and 2,2-dimethyl-1,3-dioxane-4,6-dione (701 mg, 4.86 mmol) (commercially available from Aldrich) in THF (5 mL) was then injected dropwise into the flask followed by dropwise addition of pyridine (1.8 mL, 22.1 mmol). The reaction temperature was allowed to warm to room temperature and the mixture was stirred overnight. The reaction was then quenched with water, extracted with EtOAc, dried over MgSO4, and filtered. The solvent was removed and the resulting crude mixture was purified by silica gel flash chromatography (hexane:EtOAc=4:1 to 1:1) to afford 5-(1-(3-(benzyloxy)phenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 103.B (855 mg, 55% yield).

Provenance & Evidence