HCID 53815595, compound → HCID 53908178, compound

HRID 356581Notes

Reaction equation

HRID 356581 reaction equation
[Si:1]([O: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)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O: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)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 53815595HCID 53815595, compound

Product 1

HCID 53908178HCID 53908178, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

1-{5'-[3"-(t-Butyldimethylsilyloxy)propyloxy]-2'-nitrophenyl}-2-propen-1-ol (4.98 g) is dissolved in chloroform (140 ml), and thereto is added active manganese dioxide (36 g), and the mixture is heated with stirring for six hours. The insoluble materials are removed by filtration, and the filtrate is concentrated, and the residue is purified by silica gel column chromatography to give 1-{5'-[3"-(t-butyidimethylsilyloxy)propyloxy]-2'-nitrophenyl}-2-propen-1-one (2.87 g).

Workup

  1. temperaturethe mixture is heated
  2. customThe insoluble materials are removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee8999e3889141799c0516a061edfd7b
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

Loading…