Potassium Hydroxide → Uniconazole

HRID 1902985Notes

Reaction equation

HRID 1902985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)\[CH:10](C(OC2C(C(C)C)CCC(C)C2)C([O-])=O)[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[OH-:35].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)\[CH:10]([OH:35])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86739294HCID 86739294, compound

Product 1

HCID 6436604UniconazoleYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 2.6 g of (-)-[(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-yl]-(-)-menthoxyacetate and 40 cc of a 95% aqueous ethanol solution containing 0.4 g of potassium hydroxide was stirred at 30° C. for one hour. The reaction mixture was poured into 200 cc of ice water and extracted with 300 cc of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting crude crystals were recrystallized from a carbon tetrachloride-n-hexane mixture to obtain 1.2 g of (-)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol: [α]D24 -16.0 (c=1, CHCl3); m.p. 170°-171° C. The NMR spectrum was the same as that of the racemate described in Reference Example 1.

Workup

  1. extractionextracted with 300 cc of ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude crystals were recrystallized from a carbon tetrachloride-n-hexane mixture

Sources & evidence

ORD record
ord-a89c5ded49da448c93cd0f0697761995
Source dataset
uspto-grants-1984_03
Patent number
US04435203

Reaction notes

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