Hydrochloric Acid → 1-(4-Fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol
Reaktionsgleichung
Br[C:2]1[C:10]2[O:9][C:8]([CH3:11])=[CH:7][C:6]=2[C:5]([F:12])=[CH:4][CH:3]=1.[CH:13](=[O:16])[CH2:14][CH3:15].Cl>O1CCCC1>[F:12][C:5]1[C:6]2[CH:7]=[C:8]([CH3:11])[O:9][C:10]=2[C:2]([CH:13]([OH:16])[CH2:14][CH3:15])=[CH:3][CH:4]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
A solution of 5.75 g (25.1 mmol) of 7-bromo-4-fluoro-2-methylbenzofuran in 90 ml of tetrahydrofuran was added dropwise to a suspension of 0.625 g (27.5 mmol) of Mg in 100 ml of boiling tetrahydrofuran and the mixture was stirred at reflux for 2.5 hours. Subsequently, it was cooled to 10° C., 2.75 ml (37.5 mmol) of propionaldehyde were added dropwise thereto and the mixture was stirred for 30 minutes. The mixture was poured into 200 ml of 1N hydrochloric acid and extracted three times with 150 ml of dichloromethane. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloro-methane/hexane 4:1). 3.6 g (55%) of 1-(4-fluoro-2-methyl-benzofuran-7-yl)-propan-1-ol were obtained as a pale yellow oil.
Aufarbeitung
- temperatureat reflux for 2.5 hours
- stirringthe mixture was stirred for 30 minutes
- extractionextracted three times with 150 ml of dichloromethane
- dry with materialAfter drying over sodium sulfate concentration
- customThe crude product obtained
- customwas purified by column chromatography on silica gel (dichloro-methane/hexane 4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-f36c733d391b4cd5a621cfbefcd38de5
- Quelldatensatz
- uspto-grants-1999_09
- Patentnummer
- US05955495
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