Water → HCID 178509718, Verbindung

HRID 35915

Reaktionsgleichung

Reaktionsgleichung von HRID 35915
[NH:1]1[CH:5]=[N:4][C:3]([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[N:2]1.C([N-]C(C)C)(C)C.[Li+].[C:23]1(=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24]1.O>O1CCCC1>[OH:28][C:23]1([CH:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[C:3]2[N:4]=[CH:5][NH:1][N:2]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8452CyclopentanoneHCID 2724682Lithium diisopropylamideHCID 178509721HCID 178509721, Verbindung

Produkt 1

HCID 178509718HCID 178509718, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5 g of 4-[1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved in 100 ml of tetrahydrofuran and combined at -50° with 20 ml of 1.5-molar solution of lithium diisopropylamide in tetrahydrofuran, stirred for 0.5 hour, further stirred for 1 hour with 2.4 g of cyclopentanone at -70°, and heated to 25°. Then water is added, the mixture is extracted twice with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 7.21 g of crude 4-[1-hydroxycyclopent-1-yl-1-(1,2,4-triazolyl)methyl]benzonitrile.

Aufarbeitung

  1. temperatureheated to 25°
  2. extractionthe mixture is extracted twice with ethyl acetate
  3. washwashed neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-674da19be2cd487683972606865f4d36
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411982

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