Reaktionsgleichung
[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)([CH3:7])[CH3:6])[CH3:2].[OH-].[K+].CS(C)=O.Br[CH2:26][CH2:27][CH2:28][Cl:29]>O>[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:26][CH2:27][CH2:28][Cl:29])([CH3:7])[CH3:6])[CH3:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
2-(1H-Indol-4-yloxy)-2-methylpropionic acid ethyl ester (0.100 g, 0.40 mmol, 1.0 eq), powdered potassium hydroxide (0.034 g, 0.61 mmol, 1.5 eq), and DMSO (3 mL) were mixed and stirred at room temperature for 10 minutes. 1-Bromo-3-chloropropane (0.12 mL, 0.191 g, 1.21 mmol, 3.0 eq) was then added to the above mixture. The reaction mixture was stirred at room temperature for another 1.5 hours before 15 mL of water was added. The mixture was extracted with ethyl acetate (2×30 mL). The organic layer was collected, combined, washed with water (6×25 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford 2-[1-(3-chloropropyl)-1H-indol-4-yloxy]-2-methylpropionic acid ethyl ester (0.127 g, yield: 97%) as a dense oily liquid, which was used for the next step without further purification.
Aufarbeitung
- additionwas added
- extractionThe mixture was extracted with ethyl acetate (2×30 mL)
- customThe organic layer was collected
- washwashed with water (6×25 mL) and brine (2×20 mL)
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-ac71b308e6764506acda086ceb619d3e
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07449478B2
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