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

HRID 35909

Reaktionsgleichung

Reaktionsgleichung von HRID 35909
[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+].[C:23]1(=[O:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.O>O1CCCC1.C(OCC)(=O)C>[OH:30][C:23]1([CH:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10400CycloheptanoneHCID 2724682Lithium diisopropylamideHCID 111481024-(1-Imidazolylmethyl)benzonitrile

Produkt 1

HCID 544731204-[1-Hydroxycyclohept-1-yl-1-(imidazolyl)methyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

10 g of 4-[1-(imidazolyl)methyl]benzonitrile is dissolved in 270 ml of tetrahydrofuran and combined at -50° with 40 ml of 1.5-molar solution of lithium diisopropylamide in tetrahydrofuran, stirred for 0.5 hour at -60° combined with 6 5 g of cycloheptanone, stirred further for 1 hour, and heated to 25°. Then water is added, the mixture is diluted with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus producing 16 g of crude 4-[1-hydroxycyclohept-1-yl-1-(imidazolyl)methyl]benzonitrile.

Aufarbeitung

  1. stirringstirred further for 1 hour
  2. temperatureheated to 25°
  3. washwashed neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-56040e84280d40dc85d916d576c7d6a0
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411982

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