Hydrochloric Acid → 5-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532570

Reaktionsgleichung

Reaktionsgleichung von HRID 532570
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C([O:14][C:15]([C:17]1[CH:21]=[CH:20][O:19][CH:18]=1)=O)C.Cl>C1COCC1.C(OCC)(=O)C.O>[O:19]1[CH:20]=[CH:21][C:17]([C:15]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:14])=[CH:18]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69201Ethyl 3-furoateHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

Produkt 1

HCID 866992095-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5,6-Dihydro-cyclopenta[b]thiophen-4-one in 40 mL of THF was treated with NaH (60 percent, 0.8 g, 36.25 mmol). After the addition of Furan-3-carboxylic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(Furan-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.9 g, 38 mmol) as brown solid in 27% yield.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant precipitate was collected
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5e2c0907c9e04aee98ecf18bd0aa8f4d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853207B2

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