Dimethylformamide → Methyl 3-(4-(methylthio)phenyl)propanoate

HRID 2117910Notes

Reaction equation

HRID 2117910 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC.CN([CH:24]=[O:25])C>>[CH3:13][S:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:25][CH3:24])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5797844-Mercaptohydrocinnamic Acid

Product 1

HCID 21914741Methyl 3-(4-(methylthio)phenyl)propanoate

Procedure

3-(4-Mercaptophenyl)propanoic acid (5 g), K2CO3 (11.4 g) and DMF (30 ml) were combined, and iodomethane (5.12 ml) was added dropwise to the mixture at 0° C. under N2 atmosphere. The reaction mixture was stirred at r.t. for 13 hours, and poured into ice-water. The mixture was extracted with AcOEt. The organic layer was washed with water (twice) and brine, dried over anhydrous MgSO4, and concentrated in vacuo to give methyl 3-[4-(methylthio)phenyl]propanoate (4.19 g) as pale yellow oil.

Workup

  1. extractionThe mixture was extracted with AcOEt
  2. washThe organic layer was washed with water (twice) and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef2cdb2bad914261acb339cc288a780d
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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