Water → methyl 2-(2-thienylthio)acetate

HRID 1597421Notes

Reaction equation

HRID 1597421 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].O>CN(C=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 5226742-Thiophenethiol

Product 1

HCID 12201118methyl 2-(2-thienylthio)acetateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophene-2-thiol (1.2 g, 10.3 mmol) in anhydrous DMF (30 mL) was added cesium carbonate (3.9 g, 12 mmol) and the resulting suspension was stirred for 15 min at ambient temperature, then treated with methyl bromoacetate (1.53 g, 10 mmol). The purple suspension was stirred for 1 h, then poured into water (30 mL) and extracted twice with 300 mL EtOAc. The combined organic extracts were washed with brine, dried, filtered, concentrated and the residue was purified via column chromatography eluting with 10% EtOAc/Hexanes to give 1.48 g (79%) of the title compound.

Workup

  1. stirringThe purple suspension was stirred for 1 h
  2. extractionextracted twice with 300 mL EtOAc
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified via column chromatography
  8. washeluting with 10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-1263f8e6962745d6ac0cb9b0e2d826d8
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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