Hydroxyamine hydrochloride → HCID 87950639, compound

HRID 2299708Notes

Reaction equation

HRID 2299708 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>C(O)C>[OH:19]/[N:18]=[C:2](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 4164781ethyl 5-oxo-5-phenylpentanoate

Product 1

HCID 87950639HCID 87950639, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-oxo-5-phenylpentanoate (8.00 g), hydroxylamine hydrochloride (3.03 g), sodium acetate (4.47 g) and ethanol (70 ml) was heated under reflux for 15 hours. The reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and ethyl E-5-hydroxyimino-5-phenylpentanoate (7.55 g, yield 88%) was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from hexane gave colorless crystals. m.p. 28-30° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1611f4eb858f47bfa80786ee3a66d79d
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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