Hydrochloric Acid → 4,4-Difluoro-1-[2-cyclohexenyl]-butane-1,3-dione

HRID 441043

Reaktionsgleichung

Reaktionsgleichung von HRID 441043
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[C:12]([C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1)(=[O:14])[CH3:13].Cl>CCOCC>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:13][C:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1)=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 136121-AcetylcyclohexeneHCID 10942334Sodium Methoxide

Produkt 1

HCID 189203604,4-Difluoro-1-[2-cyclohexenyl]-butane-1,3-dioneAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ethyl difluoroacetate (4.71 g, 38 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (20 mL). To the stirred solution was added 25 weight % sodium methoxide (9.68 g, 45 mmol) followed by 1-acetyl-1-cyclohexene (4.27 g, 34 mmol). The reaction was stirred at room temperature overnight (17.5 hours), then treated with 3N HCl (20 mL). The organic layer was collected and washed with brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a brown oil (6.48 g, 93%). 1H NMR (CDCl3) 300 MHz 15.00 (br s, 1H), 6.09 (s,1H), 5.92 (t, J=54.4 Hz,1H), 2.31 (m, 4H), 1.64 (m, 4H); 19F NMR (CDCl3) 300 MHz: -126.94; M+ 202.

Aufarbeitung

  1. customThe organic layer was collected
  2. washwashed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-65343abd29b045d89d2bd5e189f21daa
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521207

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