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

HRID 620695
Notes
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Reaction equation

HRID 620695 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 131652-Hydroxyethyl acrylateHCID 136683973-(2-Chloroethanesulfonyl)propanoyl chloride

Product 1

HCID 136683982-{[3-(2-Chloroethanesulfonyl)propanoyl]oxy}ethyl prop-2-enoateYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

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

  1. customwas placed in a reactor
  2. additionwas added dropwise
  3. extractionThe organic layer thus-extracted
  4. dry with materialwas dried over sodium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes