Water → 1-[3-(Trimethylsilyl)phenyl]ethanone oxime

HRID 1870539Notes

Reaction equation

HRID 1870539 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.[OH2:14].C([O-])(=O)C.[Na+].Cl.[NH2:21]O>CO>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5]([C:9](=[N:21][OH:14])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 117454861-(3-(Trimethylsilyl)phenyl)ethanone

Product 1

HCID 861760281-[3-(Trimethylsilyl)phenyl]ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound of Step C (8.9 g) in methanol (120 mL)/water (50 mL) was added sodium acetate (7.5 g) followed by the addition of hydroxylamine hydrochloride (3.8 g). The mixture was heated at reflux overnight, cooled to room temperature, and concentrated to an oil. The oil was mixed with water and extracted three times with methylene chloride. The combined organic phases were dried (MgSO4), concentrated, and chromatographed on silica gel with 8% ethyl acetate/hexane to afford the title compound of Step D as an oil. 1H NMR (CDCl3): δ 8.8 (br s,1H), 7.77 (s,1H), 7.5 (m,2H), 7.37 (t,1H), 2.31 (s,3H), 0.27 (s,8H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated to an oil
  4. additionThe oil was mixed with water
  5. extractionextracted three times with methylene chloride
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated
  8. customchromatographed on silica gel with 8% ethyl acetate/hexane

Sources & evidence

ORD record
ord-262c9b47a23a4b9f8a965cf404e95e9c
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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