Sodium borohydride → HCID 20539683, compound

HRID 1065641Notes

Reaction equation

HRID 1065641 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH:10]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[OH:11])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12923248HCID 12923248, compound

Product 1

HCID 20539683HCID 20539683, compoundYield 706.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.7 g (0.025 mol) of 1-(6-chloro-pyridin-2-yl-oxy)-2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-one (Example 1) were dissolved in 100 ml of methanol, and 1 g (0.025 mol) of sodium borohydride was added. The mixture was heated under reflux for 30 minutes and concentrated by distilling off the solvent in vacuo, and the residue was partitioned between chloroform and water. The organic phase was separated off, extracted again by shaking with water, dried over magnesium sulphate and concentrated. 62 g (70% of theory) of 1-(6-chloro-pyridin-2-yl-oxy)-2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-ol were obtained as a viscous oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationconcentrated
  4. distillationby distilling off the solvent in vacuo
  5. customthe residue was partitioned between chloroform and water
  6. customThe organic phase was separated off
  7. extractionextracted again
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-19d5e13f00294dfb894f361c318806ee
Source dataset
uspto-grants-1982_05
Patent number
US04330547

Reaction notes

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