Triethylamine → 2-(Azetidin-1-yl)-2-oxoethyl acetate

Participants

Reaction Steps

Azetidine (546 mg, 9.56 mmol) was dissolved in dichloromethane (20 mL) in a 50 mL round bottom flask and treated with triethylamine (1.47 mL, 10.5 mmol) stirring at ambient temperature for 30 minutes. 2-chloro-2-oxoethyl acetate (1.03 mL, 9.56 mmol) was added to the mixture dropwise. The mixture was stirred at ambient temperature for 16 hours. The precipitated salt was removed by filtration and the filtrate was washed with water. The solution was concentrated under vacuum to give 2-(azetidin-1-yl)-2-oxoethyl acetate as a brown oil. Lithium aluminum hydride (10.0 mL, 10.0 mmol, 1 M in THF) in a 100 mL round bottom flask was cooled in an ice-water bath. 2-(Azetidin-1-yl)-2-oxoethyl acetate as a 0.6 M solution in THF was added dropwise to the lithium aluminum hydride solution. The ice bath was removed and the mixture was stirred at ambient temperature for 2 hours. A mixture of 1:1 Celite®/sodium sulfate decahydrate was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was filtered and the filter cake was washed with THF. The filtrated was concentrated under vacuum to give 2-(azetidin-1-yl)ethanol as a viscous, colorless oil (504 mg).

Provenance & Evidence