Sodium borohydride → Diniconazole

HRID 1902991Notes

Reaction equation

HRID 1902991 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[C:10](/[N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)\[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[C:10](/[N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)\[CH:11]([OH:16])[C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11110117(E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one

Product 1

HCID 6436605DiniconazoleYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 cc of a methanol solution containing 3.2 g of (E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one (melting point 92°-93° C.) characterized by the NMR spectrum shown below, was added 0.5 g of sodium borohydride, while cooling in ice. The mixture was then stirred at room temperature for 3 hours and treated as in Reference Example 1 to obtain 2.6 g of the captioned compound melting at 148°-149° C.

Workup

  1. temperaturewhile cooling in ice
  2. additiontreated as in Reference Example 1

Sources & evidence

ORD record
ord-8cb1a6da61f5431eaef1a8a467463c17
Source dataset
uspto-grants-1984_03
Patent number
US04435203

Reaction notes

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