Sodium borohydride → 3,3-Dimethyl-4-fluoro-1-(6-fluoro-pyridin-2-yl-oxy)-1-(1,2,4-triazol-1-yl)-butan-2-ol

HRID 2295999Notes

Reaction equation

HRID 2295999 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:19][F:20])[C:3](=[O:18])[CH:4]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=1)[N:5]1[CH:9]=[N:8][CH:7]=[N:6]1.[BH4-].[Na+]>CO>[CH3:1][C:2]([CH3:21])([CH2:19][F:20])[CH:3]([OH:18])[CH:4]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=1)[N:5]1[CH:9]=[N:8][CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 128067943,3-Dimethyl-4-fluoro-1-(6-fluoro-pyridin-2-yl-oxy)-1-(1,2,4-triazol-1-yl)-butan-2-one

Product 1

HCID 128067953,3-Dimethyl-4-fluoro-1-(6-fluoro-pyridin-2-yl-oxy)-1-(1,2,4-triazol-1-yl)-butan-2-olYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 g (34 m moles) of 3,3-dimethyl-4-fluoro-1-(6-fluoro-pyridin-2-yl-oxy)-1-(1,2,4-triazol-1-yl)-butan-2-one (obtained as described in Example 1) were dissolved in 100 ml of methanol, and 0.7 g (17 m moles) of sodium borohydride was added. The mixture was stirred under reflux for 10 minutes and concentrated and the residue was partitioned between methylene chloride/water. The organic phase was separated off, washed with water, dried over sodium sulphate and concentrated. 9.3 g (90% of theory) of waxy 3,3-dimethyl-4-fluoro-1-(6-fluoro-pyridin-2-yl-oxy)-1-(1,2,4-triazol-1-yl)-butan-2-ol were obtained.

Workup

  1. temperatureunder reflux for 10 minutes
  2. concentrationconcentrated
  3. customthe residue was partitioned between methylene chloride/water
  4. customThe organic phase was separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-08a5097816e84dd79bf4068bf8f655e6
Source dataset
uspto-grants-1984_01
Patent number
US04427672

Reaction notes

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