Tetrahydrofuran → 2-[4-(2-Chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid
Reaktionsgleichung
C[O:2][C:3](=[O:24])[CH:4]([N:10]1[CH2:14][C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:12][C:11]1=[O:23])[CH2:5][C:6]([F:9])([F:8])[F:7].O1CCCC1.O.[OH-].[Li+]>O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:13]1[CH2:14][N:10]([CH:4]([CH2:5][C:6]([F:9])([F:8])[F:7])[C:3]([OH:24])=[O:2])[C:11](=[O:23])[CH:12]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A mixture of 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid methyl ester (212 mg, 0.58 mmol) in a 1:1 solution of tetrahydrofuran:water (8 mL) was treated with lithium hydroxide monohydrate (55 mg, 1.16 mmol) and stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with water (10 mL) and the pH adjusted to pH=4 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layers were then dried over sodium sulfate and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid (149 mg, 73%) as a white solid: HR-ES-MS m/z calculated for C14H11NO4ClF3 [M+Na]+ 372.0221, observed 372.0224.
Aufarbeitung
- concentrationAfter such time, the mixture was concentrated in vacuo
- customto remove the tetrahydrofuran
- additiondiluted with water (10 mL)
- extractionextracted with ethyl acetate
- dry with materialThe organic layers were then dried over sodium sulfate
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-be9a41f4a48f4aa2b47d5412ba70ab13
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07741327B2
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