Sodium borohydride → HCID 67441444, compound

HRID 1471490Notes

Reaction equation

HRID 1471490 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[C:5]([CH:20]=[O:21])[CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[C:5]([CH2:20][OH:21])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86636417HCID 86636417, compound

Product 1

HCID 67441444HCID 67441444, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(4-cyano-2-formylphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (3.00 g, 10.8 mmol) in methanol (100 mL) was added sodium borohydride (400 mg, 10.8 mmol) portionwise at 0° C., and the mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to a half volume, 1 M HCl (50 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was treated with ethyl acetate/hexane to give 5-[4-cyano-2-(hydroxymethyl)phenoxy]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (1.83 g, 60%).

Workup

  1. customThe solvent was removed under reduced pressure to a half volume, 1 M HCl (50 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. additionthe residue was treated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-5009212ee58a461bb99df77eef8ae0e8
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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