Hydroxyamine hydrochloride → Methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate

HRID 2260745Notes

Reaction equation

HRID 2260745 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=O)=[CH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C(=O)(O)[O-].[Na+]>CO.O>[OH:28][N:27]=[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 53769085Methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate

Product 1

HCID 85301016Methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoateYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 24.5 g of methyl 4,5-bis(4-methoxyphenyl)-5-oxo-3-pentenoate and 51.5 g of hydroxylamine hydrochloride in a mixture of 650 ml of methanol and 72 ml of water was heated under reflux for 23 hours. During this procedure, 0.9 equivalent of sodium bicarbonate was added portionwise to the reaction mixture as the reaction progressed. After completion of the reaction, methanol was evaporated under reduced pressure. Water and ethyl acetate were added to the residue for dissolution thereof, the organic layer was separated, washed with saturated brine and dried over anhydrous magnesium sulfate. The organic layer was then concentrated under reduced pressure and the residue was separated and purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give 23 g (yield 90%) of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 23 hours
  3. customwas evaporated under reduced pressure
  4. additionWater and ethyl acetate were added to the residue for dissolution
  5. customthe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe organic layer was then concentrated under reduced pressure
  9. customthe residue was separated
  10. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-6d717a43f9ff4eea89305759d44550fe
Source dataset
uspto-grants-1995_12
Patent number
US05478856

Reaction notes

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