Acetic Acid → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol

HRID 579761Notes

Reaction equation

HRID 579761 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)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(O)(=O)C>CO>[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

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 540228171-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

Product 1

HCID 917371-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-olYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The II-A isomer (2.9 g, 0.01 mole; m.p. 108°-109° C.) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-1-pentene-3-one (Compound No. 1') was dissolved in methanol (50 ml). Sodium borohydride (0.38 g, 0.01 mole) was added thereto while keeping the temperature of the reaction solution at 20° C. or less with ice-cooling. The reaction mixture was kept at 20° C. for 3 hours, and then decomposed with addition of water (100 ml) and acetic acid (1 ml). The organic layer was extracted with ethyl acetate (100 ml), and the extract was washed with a 5% aqueous sodium hydrogen carbonate solution (50 ml) and dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure, and the residue obtained was recrystallized from isopropanol to obtain 2.0 g (yield 69%) of the I'-A isomer having a melting point of 153°-155° C. The elementary analysis and NMR spectrum of the compound are shown below.

Workup

  1. customat 20° C. or less
  2. temperaturecooling
  3. extractionThe organic layer was extracted with ethyl acetate (100 ml)
  4. washthe extract was washed with a 5% aqueous sodium hydrogen carbonate solution (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed under reduced pressure
  7. customthe residue obtained
  8. customwas recrystallized from isopropanol
  9. customto obtain 2.0 g (yield 69%) of the I'-A isomer

Sources & evidence

ORD record
ord-ad1bb8b54d5347bdb962993426138355
Source dataset
uspto-grants-1988_06
Patent number
US04749716

Reaction notes

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