Methanol → 2-[2-(Diethylamino)ethylthio]ethanol

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Reaction Steps

2-(Diethylamino)ethanethiol hydrochloride (5.0 g, 29 mmol) was added to a 250 mL round-bottom flask, 20 mL methanol was added, and the solution cooled in an ice bath with stirring. Sodium hydroxide (2.34 g, 58 mmol), dissolved in water (15 mL), was added, followed by slow addition of 2-bromoethanol (5.9 g, 47 mmol). Stirring was continued while the reaction mixture was allowed to warm to room temperature overnight. The methanol and water were removed under reduced pressure, and the residue dissolved in ethyl acetate (100 mL), washed with water (3×20 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give 2-[2-(diethylamino)-ethylthio]ethanol as a yellow oil (4.5 g, 87% yield). LC-MS (ES+): m/z=178 [C8H19NOS+H+] for product peak. A 1.0 g aliquot of the crude 2-[2-(diethylamino)ethylthio]ethanol was purified by flash chromatography on silica cartridges, eluting with a gradient of 100% hexane to 100% ethyl acetate over 5 minutes, to give 0.78 g pure 2-[2-(diethylamino)ethylthio]ethanol as a colorless oil after evaporation of the solvents, and the remaining 3.5 g similarly purified, eluting with a gradient of 100% hexane to 100% ethyl acetate over 20 minutes, to give an additional 3.11 g pure 2-[2-(diethylamino)ethylthio]ethanol.

Provenance & Evidence