Water → HCID 178509702, compound

HRID 846086Notes

Reaction equation

HRID 846086 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:3]=[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:4]2[N:3]=[N:2][NH:1][CH:5]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 2724682Lithium diisopropylamideHCID 1785097034-[1-(1,2,3-Triazolyl)methyl]-benzonitrile

Product 1

HCID 178509702HCID 178509702, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 g of 4-[1-(1,2,3-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 with 2.9 g of cyclohexanone for 1 hour at -70°, and heated to 25°. Then water is added, the mixture is extracted three times with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 7.6 g of crude 4-[1-hydroxycyclohex-1-yl-1-(1,2,3-triazolyl)methyl]benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-323fa4012f1d49ba8b78e1cedac634cb
Source dataset
uspto-grants-1992_08
Patent number
US05135937

Reaction notes

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