Epichlorohydrin → 4-(oxiran-2-ylmethoxy)-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxyindole (0.50 g, 3.8 mmol) in dimethylsulfoxide (10 mL) at 45° C. were added potassium hydroxide (0.43 g, 7.6 mmol) and then epichlorohydrin (1.4 g, 15.2 mmol). After being stirred at 45° C. for 4 h, the reaction mixture was diluted with a saturated solution of NH4Cl and extracted with diethyl ether (3×50 mL). The combined organic layers were dried with Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel with benzene/acetone mixtures to give the glycidyl 4-indolyl ether (compound 1a) (0.75 g, quant) as a colorless oil. See FIG. 18.

Provenance & Evidence