Methanol → ethoxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetic acid
Reaktionsgleichung
[OH:1][CH:2]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]([O:5]CC)=[O:4].[OH-].[K+].O1CC[CH2:28][CH2:27]1.CO>O>[CH2:27]([O:1][CH:2]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:3]([OH:5])=[O:4])[CH3:28]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A solution of ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate (8b) (20 mg, 0.055 mmol) and potassium hydroxide (50 mg, 0.89 mmol) in a mixture of water (2 mL), tetrahydrofuran (2 mL) and methanol (0.5 mL) was stirred at 60° C. for 12 hours. Water (10 mL) was added to the reaction mixture which was washed with diethyl ether (10 mL). The aqueous layer was acidified to pH 2 with an aqueous solution of hydrochloric acid 0.5N and extracted with dichloromethane. The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (dichloromethane/ethanol) to afford unexpected ethoxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetic acid (example 8) (5.3 mg, 0.017 mmol, 31%).
Aufarbeitung
- washwas washed with diethyl ether (10 mL)
- extractionextracted with dichloromethane
- washThe organic layer was washed with brine (10 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by preparative TLC (dichloromethane/ethanol)
Quellen und Nachweise
- ORD-Eintrag
- ord-e41a743f8c3f4490901df59f491937d9
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09238026B2
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