Lithium Hydroxide → 5-(3-Chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
182 mg (0.50 mmol) of the compound from Example 17A are provided in 2 ml of dioxane, and 4.4 ml (8.80 mmol) of a 2N aqueous lithium hydroxide solution are added. The mixture is stirred at 50° C. for 2 hours and subsequently concentrated. The residue is diluted with water, a concentrated aqueous HCl solution is added until an acidic pH is obtained and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 159 mg (95% of theory) of the title compound are obtained.
Aufarbeitung
- concentrationsubsequently concentrated
- additionThe residue is diluted with water
- additiona concentrated aqueous HCl solution is added until an acidic pH
- customis obtained
- extractionthe mixture is extracted with dichloromethane
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-b2ecb932acf143009bc64aad17843aea
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08546438B2
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