Methyl Acrylate → Methyl 3-(phenylsulfanyl)propanoate

HRID 978063Notes

Reaction equation

HRID 978063 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 μl, 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-32efc6d138b347daa7d6f31bba07487a
Source dataset
uspto-grants-1987_05
Patent number
US04663336

Reaction notes

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