Sulfuric Acid → HCID 11579411, compound

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol (200 mg) and phenyl sulfonamide (1.35 g) in THF (15 mL) was added dropwise a sulfuric acid solution in THF (2 drops, 98% sulfuric acid, 5 mL THF). The mixture was allowed to stir 30 minutes at 0° C. and then at room temperature for another 30 minutes. The solution was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate (2×10 mL). The combined organic solutions were washed with water and dried over Na2SO4. Upon removal of solvents to dryness, the crude products were purified using flash column chromatography (0-20% ethyl acetate in hexanes) to yield 5,7-dimethylspiro[chromene-2,1′-cyclobutan]-6-ol as an off-white solid (106 mg).

Provenance & Evidence