Hydrochloric Acid → 6-Methoxybenzo[b]thiophene-2-ethanol
Reaktionsgleichung
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[CH:14][S:13][C:12]=2[CH:16]=1.[CH2:17]1[O:19][CH2:18]1.Cl>O1CCCC1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:15]=[C:14]([CH2:17][CH2:18][OH:19])[S:13][C:12]=2[CH:16]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -30 °C
Versuchsvorschrift
Butyl lithium (0.27 mol of a 2.5 M solution) was added dropwise to 6-methoxy-benzo[b]thiophene [prepared analogous to the procedure described in J. Med. Chem. 1989, 32(12), 2548-2554] (0.25 mol) in tetrahydrofuran (1000 ml), stirred at −30° C. The mixture was stirred for 10 minutes at −30° C. Ethylene oxide (0.38 mol in 100 ml tetrahydrofuran) was added dropwise at −30° C. The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was acidified with dilute HCl solution. The solvent was evaporated. The residue was diluted with water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was stirred in hexane, filtered off and dried, yielding 41.3 g 6-methoxybenzo[b]thiophene-2-ethanol (interm. 5).
Aufarbeitung
- customprepared analogous to the procedure
- temperatureto warm to room temperature
- stirringstirred for 3 hours
- customThe solvent was evaporated
- additionThe residue was diluted with water
- extractionthis mixture was extracted with CH2Cl2
- customThe separated organic layer was dried
- filtrationfiltered
- customthe solvent evaporated
- stirringThe residue was stirred in hexane
- filtrationfiltered off
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-9f1a0a28d1f940edab65e224616938fd
- Quelldatensatz
- uspto-grants-2003_06
- Patentnummer
- US06576640B1
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