Acetyl chloride → Methyl 5-methyl-2-thiophenecarboxylate

HRID 643777

Reaktionsgleichung

Reaktionsgleichung von HRID 643777
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8df4d6a5f3684f66becea15440d5e499
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700632B2

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