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

HRID 926757Notes

Reaction equation

HRID 926757 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 acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(mercaptomethyl)benzoic acid (500 mg, 2.97 mmol, 1.00 equiv) in acetonitrile (10.0 mL), then methyl acrylate (10.0 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.0 g, 6.57 mmol, 2.00 equiv) were added in series. The resulting solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (0˜1:6). This resulted in 220 mg (28%) of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid as a light-red oil.

Workup

  1. customInto a 50-mL round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux overnight
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. washeluted with ethyl acetate/petroleum ether (0˜1:6)
  7. customThis resulted in 220 mg (28%) of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid as a light-red oil

Sources & evidence

ORD record
ord-2761cc4ab30643df8410c4f39e4fc870
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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