Pyridine → 2-{[3-(2-Chloroethanesulfonyl)propanoyl]oxy}ethyl prop-2-enoate
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, 45.8 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-74bce4dfa3c1463ab0dfc6ee389d1ee7
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04551412
Reaction notes
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