1,2-Dichloroethane → Diclopentezol

HRID 1650350Notes

Reaction equation

HRID 1650350 reaction equation
ClCCCl.[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1/[CH:13]=[C:14](/[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)\[C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].Cl>ClCCCl.CN(C)C=O>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]=[C:14]([N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)[CH:15]([OH:20])[C:16]([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 11110117(E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one

Product 1

HCID 91738DiclopentezolYield 63.8%

Reagents, catalysts & solvents 1

HCID 20184825Dce dmfSolvent

Procedure

166 Milligrams (1.02 mmole) of the present compound obtained in Example 1 was dissolved in a 1,2-dichloroethane/dimethylformamide (27 ml/0.5 ml) mixed solvent, and 5 ml of a 1,2-dichloroethane solution containing 975 mg (3.0 mmoles) of (E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one (E/Z=94.8/5.2) was added dropwise thereto. After reaction at room temperature for 16.5 hours, 2% hydrochloric acid was added to separate the reaction solution into an aqueous and organic layers. After concentrating the organic layer, the residue was purified by column chromatography on silica gel to obtain 624 mg of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol. The ratio of the E-form alcohol to Z-form alcohol was 93.8 to 6.2, and the enantiomer ratio of the E-form alcohol was: (+)-isomer: (-)-isomer=18:82.

Workup

  1. additionwas added dropwise
  2. customAfter reaction at room temperature for 16.5 hours
  3. customto separate the reaction solution into an aqueous and organic layers
  4. concentrationAfter concentrating the organic layer
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ed641f6d31bc451c80f8de369e1e0398
Source dataset
uspto-grants-1990_05
Patent number
US04923999

Reaction notes

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