1,2-Dichloroethane → Diclopentezol

HRID 579854

Reaktionsgleichung

Reaktionsgleichung von HRID 579854
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]

Komponenten

5

Edukt 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

Produkt 1

HCID 91738DiclopentezolAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 20184825Dce dmfLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a764cf831b50408cba4033516b0467d6
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04749809

Verknüpfte Notizen

Wird geladen…