Chloroform → 1-Ethoxycarbonyl-1,1-difluoro-2-butyl methacrylate

HRID 1182643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182643
[CH2:1]([O:3][C:4](=[O:12])[C:5]([F:11])([F:10])[CH:6]([OH:9])[CH2:7][CH3:8])[CH3:2].C(Cl)(Cl)Cl.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].C(N(CC)CC)C>O>[CH2:1]([O:3][C:4]([C:5]([F:11])([F:10])[CH:6]([O:9][C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])[CH2:7][CH3:8])=[O:12])[CH3:2]

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 59863825Ethyl 2,2-difluoro-3-hydroxypentanoate

Produkt 1

HCID 598638611-Ethoxycarbonyl-1,1-difluoro-2-butyl methacrylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A 300 mL reactor was charged with 18.0 g (98.4 mmol) of 2,2-difluoro-3-hydroxypentanoic acid ethyl ester, 78 g of chloroform, 120 mg of an antioxidant NONFLEX MBP (a product of Seiko Chemical Co., Ltd.), 12.4 g (118.8 mmol/1.2 equivalents) of methacrylic acid chloride, and 15.0 g (148.8 mmol/1.5 equivalents) of triethylamine, followed by stirring at 55° C. for 4 hours. Then, 120 g of water was added, followed by extraction with chloroform one time. The obtained organic layer was washed with diluted hydrochloric acid and water, followed by removing water with magnesium sulfate, conducting a filtration, and distilling chloroform out, thereby obtaining 24.7 g of the target methacrylic acid 1-ethoxycarbonyl-1,1-difluoro-2-butyl ester. Upon this, purity was 66%, and yield was 66%.

Aufarbeitung

  1. extractionfollowed by extraction with chloroform one time
  2. washThe obtained organic layer was washed with diluted hydrochloric acid and water
  3. customby removing water with magnesium sulfate
  4. filtrationa filtration
  5. distillationdistilling chloroform out

Quellen und Nachweise

ORD-Eintrag
ord-02c45156ab084297b6e0ef17e1bf81ff
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08663903B2

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