Water → (NE)-N-[1-(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)ethylidene]hydroxylamine

HRID 1037044Notes

Reaction equation

HRID 1037044 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([C:11](=O)[CH3:12])[CH:9]=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.[NH2:16][OH:17].Cl.CC([O-])=O.[Na+].O>CO>[OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[C:11](=[N:16]/[OH:17])/[CH3:12])[CH:9]=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866854891-(1-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone

Product 1

HCID 89573865(NE)-N-[1-(1-hydroxy-3,3-dimethyl-2,1-benzoxaborol-6-yl)ethylidene]hydroxylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]-oxaborol-6-yl)ethanone (190 mg, 0.93 mmol), NH2OH HCl (77 mg, 1.12 mmol) and NaOAc (114 mg, 1.4 mmol) in MeOH (15 mL) was heated to 65° C. and stirred for 3 h. Water was added and the mixture was extracted with DCM. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give (E)-1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone oxime as a white solid. It was used in the next step without further purification. MS: m/z=220.1 (M+1, ESI+).

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33bb5feadb2d4fe7a3e2ebc169279a5f
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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