Ammonium Chloride → alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol

HRID 1089167

반응식

HRID 1089167 반응식
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[Cl:12][C:13]1[C:20]([Cl:21])=[C:19]([O:22][CH3:23])[C:18]([O:24][CH3:25])=[CH:17][C:14]=1[CH:15]=[O:16].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][N:7]1[C:11]([CH:15]([OH:16])[C:14]2[CH:17]=[C:18]([O:24][CH3:25])[C:19]([O:22][CH3:23])=[C:20]([Cl:21])[C:13]=2[Cl:12])=[CH:10][CH:9]=[N:8]1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 702551H-Pyrazole, 1-methyl-HCID 147486342,3-Dichloro-4,5-dimethoxybenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 14748635alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol수율 90.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

18 ml of 1.6M n-butyl lithium in n-hexane is added dropwise to a solution of 2.26 g of 1-methyl-pyrazole in tetrahydrofuran at -60° C. under argon gas atmosphere and the mixture is stirred at the same temperature for 1 hour. A solution of 5.88 g of 2,3-dichloro-4,5-dimethoxybenzaldehyde in tetrahydrofuran is added dropwise to the mixture at -60° to -50° C. and the mixture is stirred at -50° C. to room temperature for 1 hour. An aqueous ammonium chloride solution is added to the reaction mixture and the mixture is concentrated to remove organic solvent. The residue is extracted with ethyl acetate, and the extract is washed, dried and evaporated to remove solvent. The residue is crystallized from isopropyl ether to give 7.18 g of α-(1-methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol.

후처리

  1. stirringthe mixture is stirred at -50° C. to room temperature for 1 hour
  2. concentrationthe mixture is concentrated
  3. customto remove organic solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is crystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-06102864382144748159a39cb0e918f3
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04965282

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