Lithium borohydride → [2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol
Reaktionsgleichung
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:13]=[C:14]([C:15](OC)=[O:16])[C:7]=2[N:6]=1.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:13]=[C:14]([CH2:15][OH:16])[C:7]=2[N:6]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 55 °C
Versuchsvorschrift
A mixture of methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate (1.00 g, 2.30 mmol), lithium borohydride (100 mg, 4.60 mmol) and tetrahydrofuran (20 ml) was heated at 55° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 30% ethyl acetate/n-hexane to give 920 mg (2.26 mmol, 98%) of the title compound as a white powder.
Aufarbeitung
- concentrationThe reaction mixture was concentrated in vacuo
- additionThe residue was diluted with aqueous saturated sodium bicarbonate
- extractionextracted with ethyl acetate
- washThe extracts were washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel with a 30% ethyl acetate/n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-fb001b113a6e4fd499fd55d8d436e859
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08163935B2
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