Sodium borohydride → HCID 67439736, compound

HRID 1483632Notes

Reaction equation

HRID 1483632 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-d70d7814e7c94aab856df1c499d21414
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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