ETHYL 2,2-DIMETHOXYETHYLCARBAMATE Chemical Properties

Boiling point:

62-63 °C(Press: 0.2 Torr)

Density 

1.0823 g/cm3

storage temp. 

2-8°C, protect from light

pka

12.61±0.46(Predicted)

Appearance

Colorless to light yellow Liquid

ETHYL 2,2-DIMETHOXYETHYLCARBAMATE Usage And Synthesis

Synthesis

General procedure: Ethyl chloroformate (4.37 mL, 45.77 mmol) was slowly added dropwise to a dichloromethane/water (25/12 mL) mixture containing aminoacetaldehyde dimethyl acetal (5 mL, 45.77 mmol) and sodium hydroxide (2.05 g, 51.26 mmol) under ice bath cooling conditions, ensuring that the temperature in the reaction system was maintained at less than 10°C. The reaction was carried out at room temperature with vigorous stirring. After dropwise addition, cooling was stopped and the reaction mixture was stirred vigorously at room temperature. Upon completion of the reaction, the organic and aqueous phases were separated, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford ethyl 2,2-dimethoxyethylcarbamate as a colorless oil (8.1 g, quantitative yield). Mass spectrum (m/z): 178.1 [M+H]+.

References

[1] Patent: WO2017/21920, 2017, A1. Location in patent: Paragraph 0625; 0626
[2] Patent: WO2013/14448, 2013, A1. Location in patent: Page/Page column 99; 100
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2491 - 2496
[4] Patent: US4990517, 1991, A
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2891 - 2894

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