Acetic Acid → Uniconazole

HRID 1902990Notes

Reaction equation

HRID 1902990 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+].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

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10913254(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one

Product 1

HCID 6436604UniconazoleYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol, was dissolved 2.9 g (0.01 mole) of (E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one (melting point 108°-109° C.) characterized by the NMR spectrum given below. To the solution was added 0.38 g (0.01 mole) of sodium borohydride, while keeping the temperature of the reaction system at 20° C. or below by cooling in ice. To the solution, after having been kept at 20° C. for 3 hours, was added 1 ml of acetic acid to effect decomposition. The organic layer was extracted with 100 ml of ethyl acetate and the extract was washed with 50 ml of a 5% aqueous hydrogencarbonate solution, and dried over anhydrous sodium sulfate. After the removal of the solvent by distillation under reduced pressure, the residue was recrystallized from n-hexane to obtain 2.0 g (69% yield) of the captioned compound having a melting point of 153°-155° C. The elementary analysis and NMR spectrum (determined on a solution in deuterochloroform and expressed in terms of δ value) of each compound were as shown below:

Workup

  1. customat 20° C. or below
  2. temperatureby cooling in ice
  3. extractionThe organic layer was extracted with 100 ml of ethyl acetate
  4. washthe extract was washed with 50 ml of a 5% aqueous hydrogencarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter the removal of the solvent
  7. distillationby distillation under reduced pressure
  8. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-0984955b67d94d2db32fd037c0af97c3
Source dataset
uspto-grants-1984_03
Patent number
US04435203

Reaction notes

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