Water → HCID 178509701, compound

HRID 35923Notes

Reaction equation

HRID 35923 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: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:4]2[N:3]=[N:2][NH:1][CH:5]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8452CyclopentanoneHCID 2724682Lithium diisopropylamideHCID 1785097034-[1-(1,2,3-Triazolyl)methyl]-benzonitrile

Product 1

HCID 178509701HCID 178509701, compoundYield 97.5%

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 -60° with 20 ml of 1.5-molar solution of lithium diisopropylamide in tetrahydrofuran, stirred for 0.5 hour, further stirred for 1 hour at -70° with 2.4 g of cyclopentanone, and heated to 25°. Then the mixture is combined with water, extracted three times with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 7.1 g of crude 4-[1-hydroxycyclopent-1-yl-1-(1,2,3-triazolyl)methyl]benzonitrile.

Workup

  1. temperatureheated to 25°
  2. extractionextracted 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-bc63dccd24bb4632b0dd99bc3366851d
Source dataset
uspto-grants-1995_05
Patent number
US05411982

Reaction notes

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