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

HRID 391579Notes

Reaction equation

HRID 391579 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH:14]1N=CN(C(N2C=NC=C2)=O)C=1.CO>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 38010983-[4-(Methylsulfanyl)phenyl]propanoic acid

Product 1

HCID 21914741Methyl 3-(4-(methylthio)phenyl)propanoateYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 100 mL round bottom flask, 3-(4-(methylthio)phenyl)propanoic acid (1.00 g, 5.10 mmol) was dissolved in DMF (17 mL) under N2(g). CDI (1.24 g, 7.65 mmol) was then added to the reaction mixture and the resulting mixture was allowed to stir at room temperature for ˜45 min. MeOH (6 mL) was then added in dropwise fashion to the reaction. The reaction was allowed to stir for an additional 1 h, after which time it was extracted with EtOAc (3×50 mL) and brine (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4(s), filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 100% EtOAc) to give the title compound (0.771 g, 72%).

Workup

  1. stirringto stir for an additional 1 h
  2. extractionafter which time it was extracted with EtOAc (3×50 mL) and brine (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, gradient elution mixture: 10% EtOAc in Hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-ef6c35936f4747f78a969eae6981acf6
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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