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

HRID 745751Notes

Reaction equation

HRID 745751 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>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

5

Reactant 3

HCID 1049PyridineHCID 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 8028TetrahydrofuranSolvent2×

Procedure

600 ml of tetrahydrofuran, 45.8 g of hydroxyethyl acrylate and 72 g of 3-(2-chloroethylsulfonyl)propionic acid chloride were put into a reaction vessel. A solution containing 31.2 g of pyridine dissolved in 100 ml of tetrahydrofuran was added to the mixture dropwise over a period of 1.75 hours at a temperature below 5° C. under cooling with ice water. Then the mixture was stirred for 2 hours at room temperature and the reaction mixture was poured into 2.5 liter of ice water. The mixture was extracted four times with each of 300 ml of chloroform. The organic solvent layer was dried with sodium sulfate and concentrated to obtain 87 g of 2-[3-(chloroethylsulfonyl)propioyloxy]ethyl acrylate (yield: 88%).

Workup

  1. additionwas added to the mixture dropwise over a period of 1.75 hours at a temperature below 5° C.
  2. extractionThe mixture was extracted four times with each of 300 ml of chloroform
  3. dry with materialThe organic solvent layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e92bc7d0edc5493fb960834669cd77a5
Source dataset
uspto-grants-1986_07
Patent number
US04600687

Reaction notes

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