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Sodium Bicarbonate → 4-(3-Cyano-5-hydroxymethylindol-1-yl)benzoic acid ethyl ester

HRID 1258224
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1258224
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20](O)=[O:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].B.O1CCCC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH2:20][OH:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2]
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Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 58437256HCID 58437256, Verbindung

Produkt 1

HCID 584373394-(3-Cyano-5-hydroxymethylindol-1-yl)benzoic acid ethyl esterAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-carboxy-3-cyanoindol-1yl)benzoic acid ethyl ester (0.057 g) in tetrahydrofuran (2 mL) was added borane-tetrahydrofuran complex (1.2 mol/L tetrahydrofuran solution 0.2 mL) at 0° C. and this mixture was stirred at room temperature for 2 hours. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution, this mixture was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/1) to give the title compound (0.032 g).

Aufarbeitung

  1. extractionthis mixture was extracted with diethyl ether
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-6e1ff282085342a4a4f031058c7aeaaa
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466152B2

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