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

HRID 129210

Reaktionsgleichung

Reaktionsgleichung von HRID 129210
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[C:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])[CH3:13].Cl>CCOCC>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:13][C:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 69202-AcetylthiopheneHCID 9961Ethyl difluoroacetateHCID 10942334Sodium Methoxide

Produkt 1

HCID 170248414,4-Difluoro-1-[2-thienyl]-butane-1,3-dioneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ethyl difluoroacetate (1.84 g, 14.8 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (5 mL). To the stirred solution was added 25 weight % sodium methoxide (3.39 g, 15.7 mmol) followed by 2-acetylthiophene (1.72 g, 13.6 mmol). The reaction was stirred at room temperature overnight (15.67 hours), then treated with 3N HCl (8 mL). The organic layer was collected and washed with brine, dried over MgSO4, concentrated in vacuo, and recrystallized from methylene chloride/isooctane to give a brown solid (1.38 g, mp 78°-80° C., 50%). 1H NMR (CDCl3) 300 MHz 14.90 (br s, 1H), 7.80 (d, J=4.0 Hz, 1H), 7.71 (d, J=3.8 Hz, 1H), 7.19 (m, 1H), 6.41 (s, 1H), 6.04 (t, J=54.2 Hz, 1H); 19F NMR (CDCl3) 300 MHz: -126 98 (d); M+204.

Aufarbeitung

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customrecrystallized from methylene chloride/isooctane

Quellen und Nachweise

ORD-Eintrag
ord-e5782932b7434d6dbf249cc08ec28498
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466823

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