Dimethylformamide → HCID 69183157, Verbindung

HRID 917373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917373
CN(C)C=O.CS([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])(=O)=O.[CH:18]1([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])O.[Na+]>O>[CH:18]1([O:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])=[O:29])=[CH:26][N:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 167940206-cyclopentyloxy-pyridine-3-carboxylic acidHCID 230202374,4-Difluoro-3-Methyl-3-Buten-1-Yl Methanesulfonate

Produkt 1

HCID 69183157HCID 69183157, VerbindungAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 5 ml of N,N-dimethylformamide were dissolved 0.42 g (2.1 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate and 0.42 g (2.0 mmol) of 6-cyclopentyloxynicotinic acid, followed by the addition of 0.35 g (4.2 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (diisopropyl ether: hexane=1:7) to obtain 0.44 g (yield: 70%) of 4,4-difluoro-3-methyl-3-butenyl 6-cyclopentyloxynicotinate.

Aufarbeitung

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (diisopropyl ether: hexane=1:7)

Quellen und Nachweise

ORD-Eintrag
ord-cee816673ac644dfae89468513912f37
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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