Acetyl chloride → Methyl 5-methyl-2-thiophenecarboxylate

HRID 899503Notes

Reaction equation

HRID 899503 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-93e3ef3af9234ef5b8cb275a9c84d31e
Source dataset
uspto-grants-2008_04
Patent number
US07355049B2

Reaction notes

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