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Water → 4-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid

HRID 502886
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 502886
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][C:5]=1[CH2:6][CH:7]([CH2:10][CH2:11][CH:12]=C)[C:8]#[N:9])([O-:3])=[O:2].I([O-])(=O)(=O)=[O:26].[Na+].ClCCl.[OH2:34]>C(#N)C.C(Cl)(Cl)(Cl)Cl.[Ru](Cl)(Cl)Cl>[C:8]([CH:7]([CH2:6][C:5]1[CH:14]=[C:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:10][CH2:11][C:12]([OH:26])=[O:34])#[N:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 23667635Sodium periodateHCID 574757192-(2-Nitro-5-phenoxy-benzyl)-hex-5-enenitrile

Produkt 1

HCID 574757204-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 61850
Ruthenium trichloride
Katalysator
HCID 5943Carbon TetrachlorideLösungsmittel
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-(2-nitro-5-phenoxy-benzyl)-hex-5-enenitrile (1.07 g, 3.31 mmol) was dissolved in a mixture of acetonitrile (10 mL) and carbon tetrachloride (10 mL). In a separate vial sodium periodate (2.84 g, 13.28 mmol) was dissolved in water (15 mL) and this solution was added to the reaction mixture followed by ruthenium trichloride (0.021 g, 0.100 mmol). The reaction mixture was stirred vigorously for 16 h, and the next morning the reaction mixture was added to a separatory funnel with dichloromethane. The organic layer washed 3 times with 1N HCl and one time with saturated brine solution. The organic layer was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure to yield a residue.

Aufarbeitung

  1. additionthis solution was added to the reaction mixture
  2. washThe organic layer washed 3 times with 1N HCl and one time with saturated brine solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto yield a residue

Quellen und Nachweise

ORD-Eintrag
ord-e20b80f29cb64dd18212cb98fdce1187
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776882B2

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