Methyl Acrylate → 3-((3-Methoxy-3-oxopropylthio)methyl)benzoic acid

HRID 1408053Notes

Reaction equation

HRID 1408053 reaction equation
[SH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].N12CCCN=C1CCCCC2>C(#N)C>[CH3:17][O:16][C:12](=[O:15])[CH2:13][CH2:14][S:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 113211893-(mercaptomethyl)benzoic acid

Product 1

HCID 434082543-((3-Methoxy-3-oxopropylthio)methyl)benzoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(mercaptomethyl)benzoic acid (500 mg, 2.97 mmol, 1.00 equiv) in acetonitrile (10.0 mL) was added methyl acrylate (10.0 mL) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.0 g, 6.57 mmol, 2.00 equiv) and the resulting solution was heated to reflux overnight. The reaction was concentrated under vacuum and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0˜1:6) to afford 220 mg (28%) of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid as light-red oil.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction was concentrated under vacuum

Sources & evidence

ORD record
ord-794b3fb73bdb4cc88aa0f99844d51bd0
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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