HCID 54389470, compound → HCID 54245016, compound

HRID 356577Notes

Reaction equation

HRID 356577 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([CH:19]([OH:22])[CH:20]=[CH2:21])[CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([C:19](=[O:22])[CH:20]=[CH2:21])[CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 54389470HCID 54389470, compound

Product 1

HCID 54245016HCID 54245016, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

1-(5'-(3"-t-Butoxycarbonylaminopropyloxy)-2'-nitrophenyl)-2-propen-1-ol (9.66 g) is dissolved in chloroform (300 ml), and thereto is added active manganese dioxide (72 g), and the mixture is refluxed. After the reaction is completed, the inorganic materials are removed by filtration through a pad of Celite, and the filtrate is concentrated, stirred at 50° C. for 6 hours, and thereto is added ethyl acetate. The mixture is washed with a saturated sodium chloride solution, and dried over sodium sulfate. The residue is purified by silica gel column chromatography to give 1-[5'-(3"-t-butoxycarbonylaminopropyloxy)-2'-nitrophenyl]-2-propen-1-one (6.01 g) as a yellow product.

Workup

  1. temperaturethe mixture is refluxed
  2. customthe inorganic materials are removed by filtration through a pad of Celite
  3. concentrationthe filtrate is concentrated
  4. additionis added ethyl acetate
  5. washThe mixture is washed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcbe8a0d0be649899d877a0d7b07af4e
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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