Potassium Carbonate → HCID 4604295, compound

HRID 1521814Notes

Reaction equation

HRID 1521814 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:21])[C:18]([OH:20])=[O:19]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:21][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117292-Bromopropionic acidHCID 23642Thioguaiacol

Product 1

HCID 4604295HCID 4604295, compoundYield 754.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxythiophenol (5.0 g, 3.56 mmol) in DMF (125 mL) is added potassium carbonate (14.76 g, 10.69 mmol, 3 Eq) at 60° C. under nitrogen. The reaction mixture is stirred for 30 minutes then bromopropionic acid (6.0 g, 3.92 mmol, 1.1 Eq) is added and the resulting mixture is stirred for 90 minutes at 60° C. under nitrogen. The solvent is removed under reduced pressure and the residue is taken up in water then washed with EtOAc. The aqueous layer is acidified with aq. solution of HCl and the product is extracted with EtOAc. The organic layer is dried over MgSO4 and concentrated in under reduced pressure to afford 5.7 g (75%) of the title compound as a yellow oil.

Workup

  1. stirringthe resulting mixture is stirred for 90 minutes at 60° C. under nitrogen
  2. customThe solvent is removed under reduced pressure
  3. washthen washed with EtOAc
  4. extractionthe product is extracted with EtOAc
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationconcentrated in under reduced pressure

Sources & evidence

ORD record
ord-08431bae44924cc79ef791d35f6b1ece
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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