Acetic Acid → HCID 53652779, compound

Participants

Reaction Steps

2.5 ml of glacial acetic acid was added to a solution of 3.37 g of tert-butyl (2-hydroxy-1,1-bismethylthio-1,2,3,4-tetrahydrocarbazol-2-yl)acetate, as obtained in Example 1, in 40 ml of xylene. The reaction mixture was subsequently refluxed for 1 hour and then neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was 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 80 g of silica gel with a 19:1 v/v mixture of benzene and ethyl acetate as the eluent, to yield 2.40 g of the title compound, melting at 137°-138° C., 50 mg of 2-hydroxy-1-methylthiocarbazole (melting at 138°-140° C.), 85 mg of tert-butyl (2-hydroxy-1-oxo-1,2,3,4-tetrahydrocarbazol-2-yl)acetate (melting at 156°-157° C.) and 125 mg of 3,3a,4,5,10,10b-hexahydro-3a-hydroxy-10b-methylthiofuro[2,3-a]carbazol-2-one (obtained as an amorphous solid).

Provenance & Evidence