Water → 4-[2-Hydroxyadamant-1-yl-1-(imidazolyl)methyl]benzonitrile

HRID 846075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846075
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.C([N-]C(C)C)(C)C.[Li+].[CH:23]12[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[C:24]1=[O:33])[CH2:30]2.O>O1CCCC1>[OH:33][CH:24]1[CH:23]2[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][C:25]1([CH:6]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)[C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)[CH2:26]3)[CH2:30]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 64151AdamantanoneHCID 2724682Lithium diisopropylamideHCID 111481024-(1-Imidazolylmethyl)benzonitrile

Produkt 1

HCID 199395244-[2-Hydroxyadamant-1-yl-1-(imidazolyl)methyl]benzonitrileAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5.0 g of 4-[1-(imidazolyl)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 at -60°, combined with 4.3 g of 2-adamantanone, further stirred for 1 hour, and heated to 25°. Then water is added, the mixture is extracted three times with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 6.66 g of crude 4-[2-hydroxy-adamant-1-yl-1-(imidazolyl)methyl]benzonitrile.

Aufarbeitung

  1. stirringfurther stirred for 1 hour
  2. temperatureheated to 25°
  3. extractionthe mixture is extracted three times with ethyl acetate
  4. washwashed neutral with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-afca7158b1284dbc8c464c36653bdadd
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135937

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