Sodium borohydride → HCID 86724191, compound

HRID 873162Notes

Reaction equation

HRID 873162 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86724190HCID 86724190, compound

Product 1

HCID 86724191HCID 86724191, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 2-((6-chloropyridin-3-yl)oxy)-5-formylbenzonitrile (340 mg, 1.314 mmol) in methanol (5 ml), was added NaBH4 (74.6 mg, 1.972 mmol). The reaction mixture was stirred at rt for 30 min, and then quenched by water and extracted with EA twice. The organic phase was washed with brine, dried over Na2SO4 and evaporated in vacuo to give crude product 2-((6-chloropyridin-3-yl)oxy)-5-(hydroxymethyl)benzonitrile (240 mg, 0.921 mmol, 70.0% yield) as brown oil.

Workup

  1. customquenched by water
  2. extractionextracted with EA twice
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b06b047f1e4048a98d429fa245e46e52
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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