Ammonium Acetate → [4-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]boronic acid

HRID 1045379Notes

Reaction equation

HRID 1045379 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([B:13]3[O:17]C(C)(C)C(C)(C)[O:14]3)=[CH:9][CH:8]=2)[N:3]=1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+]>CC(C)=O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([B:13]([OH:17])[OH:14])=[CH:11][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 592323905-Methyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,4-oxadiazole

Product 1

HCID 22277087[4-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]boronic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of the product obtained in Step D above (6.5 g, 22.7 mmol) in 230 ml of acetone is stirred for 24 hours in the presence of 18.4 g (86.0 mmol) of sodium meta-periodate and 70 ml of aqueous 1M ammonium acetate solution. The acetone is evaporated off using a rotary evaporator and, after adding water, the reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed (NaCl) and dried (MgSO4) to yield, after evaporation, the expected product.

Workup

  1. customThe acetone is evaporated off
  2. customa rotary evaporator
  3. additionafter adding water
  4. extractionthe reaction mixture is extracted with ethyl acetate
  5. washwashed (NaCl)
  6. dry with materialdried (MgSO4)
  7. customto yield
  8. customafter evaporation

Sources & evidence

ORD record
ord-d7c0e318d44b4eaca00679fea41bfb3d
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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