Hydroxyamine hydrochloride → 2,1-Benzoxaborole-5-carboxaldehyde, 1,3-dihydro-1-hydroxy-3,3-dimethyl-, oxime

HRID 532152Notes

Reaction equation

HRID 532152 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1.[NH2:15][OH:16].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[N:15][OH:16])=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 768474911-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde

Product 1

HCID 866850452,1-Benzoxaborole-5-carboxaldehyde, 1,3-dihydro-1-hydroxy-3,3-dimethyl-, oximeYield 102.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (560 mg, 2.95 mmol) and NH2OH.HCl (246 mg, 3.54 mmol) in THF (6 mL) and H2O (1.5 mL) at rt was added NaOAc (339 mg, 4.13 mmol). The reaction mixture was stirred at rt for 16 h, diluted with H2O and extracted with EA (10 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product (620 mg, 100% yield) as a white solid.

Workup

  1. extractionextracted with EA (10 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8c0efb8303849a9b64420c5ad46810f
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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