Sodium borohydride → HCID 67439736, compound

HRID 1471482Notes

Reaction equation

HRID 1471482 reaction equation
C[C:2]1[C:9]([OH:10])=[C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([B:18]3[O:22][C:21](C)(C)C(C)(C)[O:19]3)=[C:14](C=O)[CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+]>CO>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[CH:14][C:15]3[B:18]([OH:19])[O:22][CH2:21][C:16]=3[CH:17]=2)=[C:9]([OH:10])[CH:2]=1)#[N:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86636414HCID 86636414, compound

Product 1

HCID 67439736HCID 67439736, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(3-formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-3-hydroxybenzonitrile (25.1 g) in methanol (300 mL) was added sodium borohydride (2.45 g, 64.5 mmol) portionwise at 0° C. The mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to about a third of volume. The mixture was acidified with 6 M HCl, and 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 purified by silica gel chromatography (7:3 to 6:4 hexane/acetone) followed by recrystallization from acetone/water and trituration with ethyl acetate to give 5-(4-cyano-2-hydroxyphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (10.9 g, 63%).

Workup

  1. customThe solvent was removed under reduced pressure to about a third of volume
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel chromatography (7:3 to 6:4 hexane/acetone)
  7. customfollowed by recrystallization from acetone/water and trituration with ethyl acetate

Sources & evidence

ORD record
ord-2afdff588aaf4564912b20f85ad4ac61
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

Loading…