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

HRID 978385Notes

Reaction equation

HRID 978385 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); 5.3 (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-d2599ebd9b6442798acddca091e05da9
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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