Sodium borohydride → Ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate

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Reaktionsgleichung

[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:6]2[CH3:20].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][OH:19])=[CH:16][CH:17]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:6]2[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of 0.90 g (2.52 mmol) of ethyl 4-chloro-6-[4-formylphenoxy)-1-methyl-2-indolecarboxylate, 0.10 g (2.52 mmol) of sodium borohydride and 20 ml of ethanol was stirred at 0° C. for 2 hours. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.91 g (>99%) of ethyl 4-chloro-6-[4-(hydroxymethyl)phenoxy]-1-methyl-2-indolecarboxylate.

Aufarbeitung

additionThe reaction mixture was poured onto ice water
extractionThe resulting mixture was then extracted three times with ethyl acetate
washThe combined extracts were washed with saturated sodium chloride aqueous solution
dry with materialAfter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-649eb4e8e0bf4abaa87cb28f49e40fd4
Quelldatensatz: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06248772B1

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