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

HRID 579765Notes

Reaction equation

HRID 579765 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-a586a20d728b41468d4ec7dd0178645a
Source dataset
uspto-grants-1988_06
Patent number
US04749716

Reaction notes

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