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Methyl iodide → 1-(4-Chlorophenyl)-4,4-dimethyl-3-methoxy-2-(1,2,4-triazole-1-yl)-1-pentene

HRID 1583709
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HRID 1583709 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([O:15][CH3:23])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 917371-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol

생성물 1

HCID 541861491-(4-Chlorophenyl)-4,4-dimethyl-3-methoxy-2-(1,2,4-triazole-1-yl)-1-pentene수율 76.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The I'-A isomer (2 g) of 1-p-chlorophenyl-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-1-pentene-3-ol (Compound No. 1) was dissolved in dimethylformamide (20 cc), and 65% oily sodium hydride (0.26 g) was added thereto. After stirring for 1 hour at room temperature, the reaction mixture was cooled to 10° C., and methyl iodide (1 g) was added. After standing at room temperature for 20 hours, the solvent was removed under reduced pressure, and the residue obtained was extracted with addition of ice water (100 g) and chloroform (100 cc). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The oily crude product obtained was purified by column chromatography on silica gel (acetone:n-hexane=1:10) and further recrystallized from a carbon tetrachloride/n-hexane (1:2) mixture to obtain 1.6 g of the entitled compound (m.p. 63°-66° C.).

후처리

  1. temperaturethe reaction mixture was cooled to 10° C.
  2. waitAfter standing at room temperature for 20 hours
  3. customthe solvent was removed under reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted with addition of ice water (100 g) and chloroform (100 cc)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe oily crude product obtained
  9. customwas purified by column chromatography on silica gel (acetone:n-hexane=1:10)
  10. customfurther recrystallized from a carbon tetrachloride/n-hexane (1:2) mixture

출처 및 근거

ORD 기록
ord-6ab8965b61724f5d9259deccb2ac426b
출처 데이터셋
uspto-grants-1985_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04554007

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