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

HRID 532144Notes

Reaction equation

HRID 532144 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 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (10 mg, 0.053 mmol) and NH2OH.HCl (4.4 mg, 0.063 mmol) in THF (4 mL) and H2O (1 mL) at rt was added NaOAc (6 mg, 0.074 mmol). The reaction mixture was stirred for 3 h and diluted with H2O. The mixture was extracted with EA and the organic layer was separated. The organic solution was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC to provide 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (8 mg; yield 74%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.23 (s, 1 H), 7.76 (d, J=7.6 Hz, 1 H), 7.55 (m, 2 H), 2.81 (s, 1 H), 1.61 (s, 6 H) ppm.

Workup

  1. extractionThe mixture was extracted with EA
  2. customthe organic layer was separated
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-4294591fd2ab417db9be4e1e82033ec5
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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