Sodium borohydride → Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-(hydroxymethyl)-1-benzothiophen-3-yl)acetate
Reaktionsgleichung
[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:23]=[C:22]([CH:24]=[O:25])[C:13]3[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:15][S:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=[C:4]([CH3:26])[N:3]=1.[BH4-].[Na+]>CO>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:14]1[C:13]2[C:22]([CH2:24][OH:25])=[CH:23][C:10]([O:9][CH2:8][C:7]3[C:2]([CH3:1])=[N:3][C:4]([CH3:26])=[CH:5][CH:6]=3)=[CH:11][C:12]=2[S:16][CH:15]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of methyl 2-(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate (140 mg, 0.38 mmol) in MeOH (3 mL) was added NaBH4 (21.51 mg) at 0° C. After stirring at 0° C. for 1 h, the mixture was quenched with saturated aqueous NH4Cl at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with saturated aqueous NH4Cl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (17.2 mg).
Aufarbeitung
- customthe mixture was quenched with saturated aqueous NH4Cl at room temperature
- extractionextracted with EtOAc
- customThe organic layer was separated
- washwashed successively with saturated aqueous NH4Cl and brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-d6542a03ae534d94acad3627bee37dbf
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09238639B2
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