Potassium Carbonate → Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate

HRID 1773809

Reaktionsgleichung

Reaktionsgleichung von HRID 1773809
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][C:2]1=O.[O:8]=[C:9]([CH3:17])[CH2:10][S:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:16][O:15][C:13]([C:12]1[S:11][C:10]([C:9](=[O:8])[CH3:17])=[C:1]2[CH2:5][CH2:4][CH2:3][C:2]=12)=[O:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5666571,2-CyclopentanedioneHCID 3761561MS-1254

Produkt 1

HCID 71014110Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylateAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Stir a mixture of Cyclopentane-1,2-dione (2.00 g, 20.4 mmol), methyl 2-(2-oxopropylthio)acetate (3.31 g, 20.4 mmol) and potassium carbonate (5.63 g, 40.8 mmol) in DMF (40 mL) at 80° C. for 4 hours. Filter off the mixture and remove the solvent under vacuum. Purify the residue by a flash column on silica gel eluting with PE:EtOAc (8:1 to 6:1) to afford 3-Acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as a pale yellow solid (206 mg, 4.5%). MS (m/z): 225 (M+1).

Aufarbeitung

  1. filtrationFilter off the mixture
  2. customremove the solvent under vacuum
  3. customPurify the residue by a flash column on silica gel eluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-a258881fc5554be2943ee9fb963efea2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255111B2

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