Triethylamine → 1-alpha-Methoxyethyl-4,4-dimethyl-azetidin-2-one

Participants

Reaction Conditions

Reaction Steps

7.3 g of triethylamine and then a mixture of 19.8 g (0.2 mole) of 4,4-dimethyl-azetidin-2-one and 43.2 g of triethylamine are added dropwise, at 0° C., to a solution of 38 g (0.4 mole) of α-chloroethyl methyl ether in 60 ml of hexane. The mixture is stirred for a further 2 hours at 0° C. and 10 ml of 50% strength sodium hydroxide solution and 20 g of powdered sodium hydroxide are added. After a further 30 minutes, the hexane solution is decanted, the deposit is rinsed with hexane and the hexane extracts are concentrated on a rotary evaporator. This yields 25.5 g (81% of theory) of 1-α-methoxyethyl-4,4-dimethyl-azetidin-2-one. 1H-NMR (CDCl3): 1.4 ppm (d); 1.5 ppm (s); 2.75 ppm (s); 3.3 ppm (s); 4.8-5.1 ppm (q).

Provenance & Evidence