2-Chloroethanol → 4-(2-chloroethoxy)-1H-indole

Participants

Reaction Conditions

Reaction Steps

To 2.0 g (1.5 mmol) 4-hydroxyindole in 50 mL THF at 0° C. is added 6.3 g (24 mmol) Ph3P, 1.51 mL (1.81 g, 22.53 mmol) 2-chloroethanol and 3.78 mL (4.19 g, 24.03 mmol) diethylazodicarboxylate. After stirring at 23° C. for 20 h, the dark reaction mixture is evaporated to a black oil. Diethyl ether (30 mL) is added, the dark solution stirred on a magnetic stir plate, and 200 mL hexanes is added (to precipitate Ph3PO). After stirring at 23° C. for 30 min, the mixture is filtered and the filtrate evaporated to a light yellow oil. Flash chromatography on SiO2 gel, eluting with hexanes/EtOAc (8/1 to 4/1), gives 1.13 g (5.78 mmol, a 39% yield) of the title compound as an off-white solid. MS (ES) m/z 196 (MH)+.

Provenance & Evidence