2-Mercaptoethanol → 2-[2-(2-Azido-Ethoxy)-Ethylsulfanyl]-Ethanol

Participants

Reaction Steps

Aqueous NaOH (3.33 g in 20 ml H2O, 1.5 equiv.) was added dropwise to a solution of tosylate 3 (15.8 g, 55.5 mmol) and β-mercaptoethanol (5.8 ml, 1.5 equiv.) in MeOH (200 ml). The resulting mixture was stirred at RT for 72 h then methanol was evaporated under reduced pressure. The resulting suspension was diluted with water (50 ml) and extracted with CH2Cl2 (6×50 ml). The combined organic layers were dried over MgSO4, filtrated then concentrated under reduced pressure. Purification by flash column chromatography (eluent: pet. ether/AcOEt 8:2 then 6:7) afforded sulfide 4 as a colorless liquid (8.41 g, 79%).

Provenance & Evidence