3-(1-hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester → Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate

HRID 1773834

Reaktionsgleichung

Reaktionsgleichung von HRID 1773834
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:13]([OH:15])[CH3:14])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:15])[CH3:14])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]

Komponenten

4

Edukt 1

HCID 710141213-(1-hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

Produkt 1

HCID 71014110Methyl 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Reflux a mixture of 3-(1-Hydroxy-ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester (3.2 g, 0.0141 mol) and manganese dioxide (10.8 g, 0.124 mol) in dichloromethane for 2 hours. Filter the hot reaction mixture solution and concentrate the filtration under vacuum. Purify the residue by silica gel chromatograph (eluting with 2% to 10% ethyl acetate in petroleum ether) to give 3-acetyl-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as white solid (3.0 g, 13.39 mmol, 94.5%). 1H NMR (CDCl3, 400 MHz): δ 3.88 (s, 3H), 2.96 (m, 4H), 2.50 (s, 3H), 2.45 (m, 2H).

Aufarbeitung

  1. temperatureReflux
  2. filtrationFilter the hot reaction mixture solution
  3. concentrationconcentrate
  4. filtrationthe filtration under vacuum
  5. customPurify the residue
  6. washby silica gel chromatograph (eluting with 2% to 10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-972fd1201164422c90563ca7be7bc606
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255111B2

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