1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,4]triazole → 4-[1,2,4]Triazol-1-yl-cyclohexanone

HRID 244914Notes

Reaction equation

HRID 244914 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1>C1COCC1.Cl>[N:11]1([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 1

HCID 574240961-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,4]triazole

Product 1

HCID 574240934-[1,2,4]Triazol-1-yl-cyclohexanone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,4]triazole (379 mg, 1.81 mmol) is dissolved in a 1:1 mixture of THF and 3N HCl aqueous solution (9 mL). The resulting mixture is stirred at 40° C. for 5 h. Most of the THF is removed under vacuum then the remaining mixture is neutralized using a 3N NaOH aqueous solution until a basic pH is reached. It is extracted with 3 portions of 10 mL of dichloromethane. The organic portions are combined, dried over anhydrous Na2SO4 and concentrated to afford 4-[1,2,4]triazol-1-yl-cyclohexanone as a white waxy solid.

Workup

  1. customMost of the THF is removed under vacuum
  2. extractionIt is extracted with 3 portions of 10 mL of dichloromethane
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a30ba43b51eb45488a0b9c4254601914
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

Loading…