Ethyl Acetate → 3,3-Diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime

HRID 1750839Notes

Reaction equation

HRID 1750839 reaction equation
[CH2:1]([C:3]1([CH2:15][CH3:16])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH:13]=O)=[CH:12][C:4]1=2)[CH3:2].[NH2:17][OH:18].Cl.CC([O-])=O.[Na+].CC(=O)OCC>C1COCC1.O>[CH2:1]([C:3]1([CH2:15][CH3:16])[O:7][B:6]([OH:8])[C:5]2[CH:9]=[CH:10][C:11]([CH:13]=[N:17][OH:18])=[CH:12][C:4]1=2)[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866850843,3-Diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde

Product 1

HCID 866850853,3-Diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oximeYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3,3-diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (1.1 g, 5.04 mmol) and NH2OH.HCl (420 mg, 6.05 mmol) in THF (20 ml) and H2O (5 ml) at rt was added NaOAc (578 mg, 7.06 mmol). The mixture was stirred at rt for 16 h, diluted with H2O and extracted with EA (20 ml×2). The combined organic layers were washed with aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (10:1 to 1:1) to give the product (600 mg, yield 51%) as white solid: MS: m/z=234 [M+1]+.

Workup

  1. extractionextracted with EA (20 ml×2)
  2. washThe combined organic layers were washed with aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE

Sources & evidence

ORD record
ord-8b0dc756317b46c9be1230b9bfc82781
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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