Reaktionsgleichung
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]=O.[CH3:13][NH2:14].[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:11][NH:14][CH3:13]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-chlorobenzofuran-2-carboxaldehyde (1.62 g, 8.9 mmol) in methanol (50 mL) is added N-methylamine (33% solution in ethanol, 1.11 g, 35.9 mmol) and stirred overnight at room temperature. The mixture is concentrated in vacuo, re-solvated in methanol (50 mL) and cooled in an ice bath. Sodium borohydride (407 mg, 10.8 mmol) is added in portions and the mixture stirred at room temperature for 4 h. The mixture is concentrated in vacuo, re-solvated in 1.3M sodium hydroxide solution, stirred for 20 min, extracted with ethyl acetate, dried with sodium sulfate and concentrated. Purification by column chromatography (silica, CH2Cl2/MeOH, 9/1) gave title compound (1.43 g, 82%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.55-7.63 (m, 2H), 7.33-7.42 (m, 2H), 3.93 (s, 2H), 2.27 (s, 3H).
Aufarbeitung
- concentrationThe mixture is concentrated in vacuo, re-solvated in methanol (50 mL)
- temperaturecooled in an ice bath
- stirringthe mixture stirred at room temperature for 4 h
- concentrationThe mixture is concentrated in vacuo, re-solvated in 1.3M sodium hydroxide solution
- stirringstirred for 20 min
- extractionextracted with ethyl acetate
- dry with materialdried with sodium sulfate
- concentrationconcentrated
- customPurification by column chromatography (silica, CH2Cl2/MeOH, 9/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-460640b88e1d4bb8977386d0a7e38603
- Quelldatensatz
- uspto-grants-2011_02
- Patentnummer
- US07879872B2
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