Water → 6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene

Participants

Reaction Conditions

Reaction Steps

1-methoxy-3-[2-(methoxymethoxy)-1,1-dimethyl-ethyl]benzene (Intermediate 40, 300 mg, 1.3375 mmol) was dissolved in DCM (8 mL), the solution was cooled to −78° C. and titanium tetrachloride (37.928 mg, 0.2000 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 2 hours. water (15 mL) was added and the mixture extracted with EtOAc (25 mL). Organics were dried over Na2SO4, filtered and evaporated to afford a crude that was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 90:10 as eluent affording the title compound (350 mg).

Provenance & Evidence