Hydrochloric Acid → 5-Benzoyl-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532541

Reaktionsgleichung

Reaktionsgleichung von HRID 532541
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C1([O:18][C:19](=O)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)C=CC=CC=1.Cl>C1COCC1.C(OCC)(=O)C.O>[C:19]([CH:7]1[CH2:8][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]1=[O:9])(=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7169Phenyl benzoateHCID 24758Sodium hydrideHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

Produkt 1

HCID 866991985-Benzoyl-5,6-dihydro-cyclopenta[b]thiophen-4-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5,6-Dihydro-cyclopenta[b]thiophen-4-one (3.34 g, 24.2 mmol) in 40 mL of THF was treated with NaH (60 percent, 1.45 g, 36.25 mmol). After the addition of Benzoic acid phenyl 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 (80 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-Benzoyl-5,6-dihydro-cyclopenta[b]thiophen-4-one (4.3 g, 17.7 mmol) as white solid in 73% 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-3106beaad0234cb4964de82aa2c0dbef
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853207B2

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