Ethanol → 3-Thiophenecarboxylic acid, ethyl ester

HRID 910279Notes

Reaction equation

HRID 910279 reaction equation
S(Cl)(Cl)=O.[S:5]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6]1.[CH2:13](O)[CH3:14]>CN(C)C1C=CN=CC=1>[S:5]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 6918Thiophene-3-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 798243-Thiophenecarboxylic acid, ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

13 ml (200 mmol) of thionyl chloride are added dropwise, at 0° C., to a solution of 9 g (70 mmol) of 3-thiophenecarboxylic acid and 86 mg (0.7 mmol) of 4-dimethylaminopyridine in 100 ml of ethanol. The reaction medium is stirred from 0° C. to room temperature over 48 hours and then evaporated to dryness. The residue obtained is purified by chromatography on a column of silica eluted with a 1/1 heptane/dichloromethane mixture. 10 g (91%) of ethyl thiophene-3-carboxylate are obtained.

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. customis purified by chromatography on a column of silica
  4. washeluted with a 1/1 heptane/dichloromethane mixture

Sources & evidence

ORD record
ord-9053dc691a1f4721bfa672638a8692b2
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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