Tributylstannane → Ethyl-4-(3-methylphenyl)butanoate

HRID 5027

Reaktionsgleichung

Reaktionsgleichung von HRID 5027
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:10](=[O:13])[CH2:11][CH2:12][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=1)[CH3:16]

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 8821Ethyl AcrylateHCID 12102m-Xylyl chloride

Produkt 1

HCID 19797639Ethyl-4-(3-methylphenyl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 14.0 g of 3-methylbenzyl chloride and 50.0 g of ethyl acrylate dissolved in 300 ml of dry toluene was heated to 110° C. Separatively, 3.0 g of 2,2'-azobisisobutyronitrile(AIBN) and 32.0 g of tri-n-butyltin hydride were dissolved in 200 ml of dry toluene, which was added to the above mixture over a period of 2 hours. This reaction mixture was further heated at the boiling temperature for 2 hours and then cooled to the ambient temperature. The residues obtained after removing the solvent from the mixture were purified by silica gel column chromatography to provide ethyl-4-(3-methylphenyl)butanoate.

Aufarbeitung

  1. additionwhich was added to the above mixture over a period of 2 hours
  2. temperatureThis reaction mixture was further heated at the boiling temperature for 2 hours
  3. temperaturecooled to the ambient temperature
  4. customThe residues obtained
  5. customafter removing the solvent from the mixture
  6. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-603826e869b34924b60f03525d155479
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242944

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