Water → HCID 178509719, Verbindung

HRID 35913

Reaktionsgleichung

Reaktionsgleichung von HRID 35913
[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:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.O>O1CCCC1>[OH:29][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)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7967CyclohexanoneHCID 2724682Lithium diisopropylamideHCID 178509721HCID 178509721, Verbindung

Produkt 1

HCID 178509719HCID 178509719, VerbindungAusbeute 94,5 %

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 agitated with 2.9 g of cyclohexanone for 1 hour at -70° and heated to 25°. Then water is added, the mixture is extracted with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 7.24 g of crude 4-[1-hydroxycyclohex-1-yl-1-(1,2,4-triazolyl)methyl]benzonitrile.

Aufarbeitung

  1. temperatureheated to 25°
  2. extractionthe mixture is extracted 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-2c14748fbf5f4e2f9927f9717f486cba
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411982

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