2-Thiopheneacetic acid → Methyl thiophen-2-acetate

HRID 1896250Notes

Reaction equation

HRID 1896250 reaction equation
S(Cl)(Cl)=O.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([OH:13])=[O:12].[C:14](=O)(O)[O-].[Na+]>CO>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 159702-Thiopheneacetic acidHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 88055Methyl thiophen-2-acetateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (10.20 ml, 140.7 mmol) was added to a solution of thiophen-2-yl-acetic acid (10.0 g, 70.3 mmol) in MeOH (100 ml) at 0° C. The reaction mixture was heated to reflux for 18 h, the volatiles were evaporated and the crude reaction mixture was basified with aqueous sodium bicarbonate solution, extracted with DCM, washed with brine and dried over anhydrous sodium sulfate. After filtration the organic solvent was evaporated and dried to afford 10.75 g (98%) of methyl 2-(thiophen-2-yl)acetate as color less liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customthe volatiles were evaporated
  4. customthe crude reaction mixture
  5. extractionextracted with DCM
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration the organic solvent
  9. customwas evaporated
  10. customdried

Sources & evidence

ORD record
ord-0fe0a6f513a2464199c894efccd192dc
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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