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

HRID 1156202Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C:9]1([CH3:14])[NH:12][C:11](=[O:13])[CH2:10]1.[CH3:15][O:16][CH:17](Cl)[CH3:18].[OH-].[Na+]>CCCCCC>[CH3:15][O:16][CH:17]([N:12]1[C:9]([CH3:14])([CH3:8])[CH2:10][C:11]1=[O:13])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

waitAfter a further 30 minutes
customthe hexane solution is decanted
washthe deposit is rinsed with hexane
concentrationthe hexane extracts are concentrated on a rotary evaporator

Sources & evidence

ORD record: ord-a266d85ce0ca46a3b4506d852701f147
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04334097

Reaction notes

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