Butyl iodide → HCID 19010813, Verbindung

HRID 1741837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741837
I[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11]>C1C=CC=CC=1.CN(C)C=O.[Cu].[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:6][O:7][C:8]1[CH:16]=[C:15]([CH:17]=[C:18]([CH3:20])[CH3:19])[CH:14]=[CH:13][C:9]=1[C:10](=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

7

Edukt 2

HCID 10962Butyl iodideHCID 190108112-Methoxy-4-(2-methyl-1-propen-1-yl)benzoyl chloride

Produkt 1

HCID 19010813HCID 19010813, VerbindungAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10290809Zinc copper coupleKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1-iodobutane (185 mg) and zinc-copper couple (101 mg) in benzene (3 ml) and N,N-dimethylformamide (0.2 ml) was stirred at 60° C. for 2 hours. To the mixture, a solution of tetrakis(triphenylphosphine)palladium (31 mg) and 2-methoxy-4-(2-methyl-1-propenyl)benzoyl chloride (prepared from 138 mg of 2-methoxy-4-(2-methyl-1propenyl)benzoic acid and 0.07 ml of oxalyl chloride) in benzene (2 ml) was added, and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and the organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (9:1) to give 2'-methoxy-4'-(2-methyl-1-propenyl)valerophenone (91 mg) 10 as an oil.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel column
  9. washeluting with a mixture of hexane and ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-083f3233553d4dbfa3c7d233603f8751
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05334716

Notizen zur Reaktion

Wird geladen…