Sodium Thiosulfate → (7-Methoxy-quinoxalin-2-ylsulfanyl)-acetaldehyde

Participants

Reaction Conditions

Reaction Steps

Dess-Martin periodinane (10.8 g, 25.4 mmol, 2.0 eq) is added at 0° C. to a stirred solution of 2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethanol (3.0 g, 12.7 mmol, 1.0 eq) in dichloromethane (100 mL). The reaction mixture is stirred 0° C. for 30 minutes then at room temperature for 3 hours. Then a saturated sodium thiosulfate aqueous solution (50 mL) is added, followed by a saturated sodium hydrogen carbonate aqueous solution (50 mL). The resulting mixture is stirred for 30 minutes, then extracted with dichloromethane (3×100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:hexane, 1:5, v/v) to afford (7-methoxy-quinoxalin-2-ylsulfanyl)-acetaldehyde as a yellow oil (2.22 g, 75% yield).

Provenance & Evidence