1H-1,2,4-Triazole → 4-[1,2,4]Triazol-1-yl-cyclohexanone

HRID 1675555Notes

Reaction equation

HRID 1675555 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](OS(C)(=O)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.[H-].[Na+]>CN(C=O)C>[N:16]1([CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:20]=[N:19][CH:18]=[N:17]1.[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([N:16]3[CH:20]=[N:19][CH:18]=[N:17]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Product 2

HCID 574240934-[1,2,4]Triazol-1-yl-cyclohexanoneHCID 574240961-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester (567 mg, 2.40 mmol) and 1,2,4-triazole (232 mg, 3.36 mmol) in dry DMF (5.00 mL) is treated with sodium hydride 60% (125 mg, 3.12 mmol) at room temperature under nitrogen. The resulting mixture is stirred at 65° C. for 72 h. It is poured in ice water (75 mL), extracted 3 portions of 75 mL of EtOAc. The organic portions are combined, dried over anhydrous Na2SO4 and concentrated. The solid is purified by silica gel column chromatography using a gradient from 100% EtOAc to 5% MeOH:EtOAc as eluent to furnish the final compound 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-[1,2,4]triazole as a white solid.

Workup

  1. extractionextracted 3 portions of 75 mL of EtOAc
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe solid is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c52bd62f6ae4f28a7ff24ed8591f2a6
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Reaction notes

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