Potassium Hydroxide → Uniconazole

HRID 1902986Notes

Reaction equation

HRID 1902986 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 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Similarly, 1.2 g of (+)-[(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-yl]-(-)-menthoxyacetate was treated with 20 cc of a 95% aqueous ethanol solution containing 0.2 g of potassium hydroxide and the resulting crude crystals were recrystallized from a carbon tetrachloride-n-hexane mixture to obtain 0.5 g of (+)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol: [α]D24 +14.0 (c=1.0, CHCl3); m.p. 169°-170° C.

Workup

  1. customthe resulting crude crystals were recrystallized from a carbon tetrachloride-n-hexane mixture

Sources & evidence

ORD record
ord-1db7c182275947e09d586988c90f2874
Source dataset
uspto-grants-1984_03
Patent number
US04435203

Reaction notes

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