Ethylene Glycol → 2-(2-Ethyl-[1,3]dioxolan-2-yl)fluoroacetic acid methyl ester

HRID 1096807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096807
[CH3:1][O:2][C:3](=[O:10])[CH:4]([F:9])[C:5](=[O:8])[CH2:6][CH3:7].[CH2:11](O)[CH2:12][OH:13].B(F)(F)F.CCOCC>C1CCCCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([F:9])[C:5]1([CH2:6][CH3:7])[O:13][CH2:12][CH2:11][O:8]1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 10219521Methyl 2-fluoro-3-oxopentanoate

Produkt 1

HCID 866370542-(2-Ethyl-[1,3]dioxolan-2-yl)fluoroacetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8078CyclohexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Fluoro-3-oxopentanoic acid methyl ester (2.21 g, 14.9 mmol), ethylene glycol (4.15 mL, 74.5 mmol), and BF3.Et2O (0.189 mL, 1.49 mmol) were mixed in cyclohexane (10 mL). The mixture was heated to reflux for 5 h, and allowed to cool to rt. The mixture was diluted with EtOAc, and washed with brine, water, aq. sat. NaHCO3, and brine again. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The title compound was obtained as an oil (1.88 g, 52%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h
  3. washwashed with brine, water, aq. sat. NaHCO3, and brine again
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5ff2c256654249219f368c1248a6f9b0
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138340B2

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