2-Cyclopenten-1-one → HCID 20202804, compound

HRID 543764Notes

Reaction equation

HRID 543764 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[C:6]1(=[O:11])[CH2:10][CH2:9][CH:8]=[CH:7]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[N:1]1[N:2]([CH:8]2[CH2:9][CH2:10][C:6](=[O:11])[CH2:7]2)[N:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 66854Benzyltrimethylammonium hydroxideHCID 178418936HCID 178418936, compound

Product 1

HCID 20202804HCID 20202804, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,2,3-triazole (3.5 g.), cyclopent-2-enone (5.0 g.), benzyltrimethylammonium hydroxide (40% w/v solution in MeOH; 2.0 ml.) and dioxan (20 ml.) was stirred at room temperature overnight. The mixture was evaporated, treated with EtOAc, washed twice with water and once with brine, dried (MgSO4), and evaporated to give unpurified 3-(1,2,3-triazol-2-yl)cyclopentanone as a pale yellow oil. The n.m.r. spectrum of the product exhibited the following resonances: 7.62 (s, 2H); 5.37 (br quintet, 1H); 3.1-1.8 (m, 6H). (solvent CDCl3)

Workup

  1. customThe mixture was evaporated
  2. additiontreated with EtOAc
  3. washwashed twice with water and once with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-df83a1e357f743d297560c16c013c94d
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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