Methyl Acrylate → Methyl 3-(phenylsulfanyl)propanoate

HRID 569942Notes

Reaction equation

HRID 569942 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17]>C(Cl)Cl>[C:1]1([S:7][CH2:17][CH2:16][C:15]([O:19][CH3:20])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 7969ThiophenolHCID 8471Triethylamine

Product 1

HCID 350367Methyl 3-(phenylsulfanyl)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thiophenol (440 mg, 4 mmol) and Et3N (70 μ1, 0.5 mmol) were dissolved in CH2Cl2 (5 ml). Methyl acrylate (412 mg, 4.8 mmol) was added dropwise. The reaction was exothermic. After stirring at room temperature for 30 minutes, the excess methyl acrylate was removed in vacuo. TLC: silica gel, Et2O-hexane 1:2, UV Rf =0.58. The crude title ester was used without further purification.

Workup

  1. customthe excess methyl acrylate was removed in vacuo
  2. customThe crude title ester was used without further purification

Sources & evidence

ORD record
ord-c85e2182699e4d24be8cca38331546e8
Source dataset
uspto-grants-1988_03
Patent number
US04734424

Reaction notes

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