Hydrogen Peroxide → 4,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1,1-dioxide

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Reaction Steps

A solution of 4,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1-oxide (148 mg, 0.67 mmol) in ethanol (5.94 mL): THF (2.40 mL) and hydrogen peroxide (2.33 mL, 26.6 mmol, 35 wt. % in water) was treated with ammonium molybdate (26.1 mg, 0.13 mmol) at room temperature. The mixture was stirred at room temperature for 80 minutes before being diluted with dichloromethane (30.0 mL) and saturated aqueous NH4Cl (5.00 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2×, 30.0 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% MeOH/dichloromethane to give the desired product as a white solid.

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