Acetyl chloride → Methyl 5-methyl-2-thiophenecarboxylate

HRID 1176760Notes

Reaction equation

HRID 1176760 reaction equation
[C:1](Cl)(=O)C.[CH3:5][C:6]1[S:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1>CO>[CH3:1][O:12][C:11]([C:9]1[S:10][C:6]([CH3:5])=[CH:7][CH:8]=1)=[O:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 747135-Methylthiophene-2-carboxylic acid

Product 1

HCID 580756Methyl 5-methyl-2-thiophenecarboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (5 mL) was added to a 0° C. solution of methanol (40 mL) and the solution was allowed to warm to room temperature. 5-Methyl-thiophene-2-carboxylic acid (Lancaster; 1.58 g, 11.1 mmol) was added and the solution was allowed to stir at room temperature over the weekend. The solvents were evaporated under reduced pressure and ethyl acetate was added. The solution was extracted with aqueous sodium hydrogen carbonate and the aqueous layer was back-extracted with ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, and evaporated to give 5-methyl-thiophene-2-carboxylic acid methyl ester (1.40 g, 81%) as a yellow oil.

Workup

  1. customThe solvents were evaporated under reduced pressure and ethyl acetate
  2. additionwas added
  3. extractionThe solution was extracted with aqueous sodium hydrogen carbonate
  4. extractionthe aqueous layer was back-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-95560d955ad542ea8bfc93b1327f0f96
Source dataset
uspto-grants-2010_11
Patent number
US07842825B2

Reaction notes

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