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

HRID 464625Notes

Reaction equation

HRID 464625 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%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a mixture of 600 ml. of tetrahydrofuran, 45.8 g. of hydroxyethyl acrylate, and 72 g. of 3-(2-chloroethylsulfonyl)propionyl chloride placed in a reaction vessel chilled with ice-water to maintain the temperature below 5° C., a solution of 31.2 g. of pyridine in 100 ml. of tetrahydrofuran was poured dropwise for 1.75 hours. The resulting mixture was stirred at room temperature for 2 hours, and poured into 2.5 l. of ice-water. The aqueous mixture was then extracted with 4 portions of 300 ml. of chloroform. The organic extract was dried over sodium sulfate, and concentrated to give 87 g. of 2-[3-(2-chloroethylsulfonyl)propionyloxy]ethyl acrylate (yield 88%).

Workup

  1. additionInto a mixture of 600 ml
  2. temperatureto maintain the temperature below 5° C.
  3. additionpoured into 2.5 l
  4. extractionThe aqueous mixture was then extracted with 4 portions of 300 ml
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give 87 g

Sources & evidence

ORD record
ord-6c95c5b46e444ab6aff6cd73a45342cd
Source dataset
uspto-grants-1985_10
Patent number
US04548870

Reaction notes

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