Ethanol → 1-Ethyl 3,3-difluoro-1,1-cyclobutanedicarboxylate

HRID 1497909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497909
[F:1][C:2]1([F:16])[CH2:5][C:4]([C:11]([O:13]CC)=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.CCO>O>[CH2:9]([O:8][C:6]([C:4]1([C:11]([OH:13])=[O:12])[CH2:3][C:2]([F:1])([F:16])[CH2:5]1)=[O:7])[CH3:10]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 67231267Diethyl 3,3-difluorocyclobutane-1,1-dicarboxylate

Produkt 1

HCID 672304401-Ethyl 3,3-difluoro-1,1-cyclobutanedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Diethyl 3,3-difluorocyclobutane-1,1-dicarboxylate (161) (2.8 g, 12 mmol) was dissolved in ice cooled ethanolic potassium hydroxide solution (0.5 M, 11 mL) and water (2.2 mL). The mixture was stirred at room temperature overnight. An additional 0.5 eq was added to the solution at room temperature and the mixture was stirred at room temperature overnight. Water was added and most of the EtOH was removed under reduced pressure. The mixture was acidified with 2M HCl and extracted three times with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to yield 1-(ethoxycarbonyl)-3,3-difluorocyclobutanecarboxylic acid (162). 1H NMR (400 MHz, CD2Cl2) δ 4.33-4.24 (m, 2H), 3.26-3.13 (m, 4H), 1.34-1.27 (m, 3H). MS m/z 209.2 (M+1)+.

Aufarbeitung

  1. additionAn additional 0.5 eq was added to the solution at room temperature
  2. stirringthe mixture was stirred at room temperature overnight
  3. customwas removed under reduced pressure
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7f057c27caf49dc90ab71670de6c5c5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199981B2

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