Pyridine → 2-{[3-(2-Chloroethanesulfonyl)propanoyl]oxy}ethyl prop-2-enoate

HRID 620695Notes

Reaction equation

[C:1]([O:5][CH2:6][CH2:7][OH:8])(=[O:4])[CH:2]=[CH2:3].[Cl:9][CH2:10][CH2:11][S:12]([CH2:15][CH2:16][C:17](Cl)=[O:18])(=[O:14])=[O:13].N1C=CC=CC=1.C(Cl)(Cl)Cl>O1CCCC1>[C:1]([O:5][CH2:6][CH2:7][O:8][C:17](=[O:18])[CH2:16][CH2:15][S:12]([CH2:11][CH2:10][Cl:9])(=[O:14])=[O:13])(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 600 ml of tetrahydrofuran, 46.8 g of hydroxyethyl acrylate, and 72 g of 3-(2-chloroethylsulfonyl)propionic acid chloride was placed in a reactor, and while maintaining the temperature at 5° C. or lower by cooling by ice water, a solution containing 31.2 g of pyridine dissolved in 100 ml of tetrahydrofuran was added dropwise thereto over a period of 1.75 hours. The resulting mixture was further stirred for 2 hours at room temperature. At the end of the time, the reaction mixture was poured into 2.5 liters of ice water, and extraction was performed four times with 300 ml of chloroform. The organic layer thus-extracted was dried over sodium sulfate and concentrated to provide 87 g of 2-[3-(chloroethylsulfonyl)propionyloxy]ethyl acrylate which was a liquid at room temperature (decomposed during distillation). Yield was 88%.

Workup

customwas placed in a reactor
additionwas added dropwise
extractionThe organic layer thus-extracted
dry with materialwas dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-9d171367da3c4afca06b925c2ea00df8
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822727

Reaction notes

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