p-Toluenesulfonic acid → HCID 53769491, compound

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Reaction Steps

680 mg of p-toluenesulfonic acid was added to a mixture of 10.6 g of 3-(4-methylthio-4-methylsulfinyl-3-oxobutene-1-yl)indole, as obtained in Example 1(b), in 150 ml of tetrahydrofuran and 40 ml of benzene. The reaction mixture was next refluxed for 3 hours and then neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The solvent was removed from the resulting mixture by evaporation under reduced pressure and ethyl acetate was added to the residue. The aqueous layer was then extracted with ethyl acetate, and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 300 g of silica gel with a 9:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 9.7 g of the title compound as an amorphous solid.

Provenance & Evidence