1,2-Dichloroethane → Diclopentezol

HRID 579854

반응식

HRID 579854 반응식
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]

참가 물질

5

반응물 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

생성물 1

HCID 91738Diclopentezol수율 63.8%

시약·촉매·용매 1

HCID 20184825Dce dmf용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a764cf831b50408cba4033516b0467d6
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04749809

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