Oxygen → tert-Butyl (9-benzyl-1-methylthiocarbazol-2-yl)hydroxyacetate

Participants

Reaction Steps

0.47 ml of a 1.0M solution of lithium hexamethyldisilazide in tetrahydrofuran was added, with ice-cooling, to a solution of 65 mg of tert-butyl (9-benzyl-1-methylthiocarbazol-2-yl)acetate, as obtained in Example 4, in 5 ml of tetrahydrofuran. The reaction mixture was then stirred for 1 hour in the presence of atmospheric oxygen. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. 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 1.5 g of silica gel with a 3:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 43 mg of the title compound as an oil.

Provenance & Evidence