Carbon Dioxide → 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid
Reaktionsgleichung
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])=[N:3]1.C([N-]C(C)C)(C)C.[Li+].[C:22](=[O:24])=[O:23].[OH-].[Na+]>C(OCC)C.C1COCC1.CCCCCCC.O>[CH3:1][N:2]1[C:6]([C:22]([OH:24])=[O:23])=[CH:5][C:4]([C:7]([F:12])([F:13])[C:8]([F:9])([F:10])[F:11])=[N:3]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
Under an argon atmosphere, 5.00 g (24.99 mmol) of 1-methyl-3-pentafluoroethyl-1H-pyrazole are initially introduced in diethyl ether and the solution is cooled to −78° C. 11.09 ml (27.73 mmol) of 2M lithium diisopropylamide solution in THF/heptane are added dropwise and, at −30° C. with vigorous stirring, 450 g of crushed dry ice are added. When the evolution of gas has finished, the reaction mixture is admixed with 235 ml of water and adjusted to a pH of 11 with 1N sodium hydroxide solution. The alkaline solution is extracted three times with ethyl acetate and then adjusted to pH 2 with 1N hydrochloric acid. The aqueous phase is extracted three times with ethyl acetate and the organic phase is dried over sodium sulphate. Distilling off the solvent on a rotary evaporator under reduced pressure gives 1.20 g (17.75% of theory) of 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid as a solid.
Aufarbeitung
- additionare added
- extractionThe alkaline solution is extracted three times with ethyl acetate
- extractionThe aqueous phase is extracted three times with ethyl acetate
- dry with materialthe organic phase is dried over sodium sulphate
- distillationDistilling off the solvent
- customon a rotary evaporator under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-a023707af7ef45beae0c96f207a2211d
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08946234B2
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