Tributylvinyltin → HCID 22935206, Verbindung

HRID 919308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919308
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[CH:12]([Sn](CCCC)(CCCC)CCCC)=[CH2:13]>C1(C)C=CC=CC=1.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>[CH:12]([C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1)=[CH2:13]

Komponenten

5

Edukt 2

HCID 81998TributylvinyltinHCID 131692632-Chloro-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 22935206HCID 22935206, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-5,6,7,8-tetrahydroquinoline (3.69 g, 22 mmol) and vinyl tributyl tin (7.7 mL, 33 mmol) in toluene (60 mL) was treated with Pd(PPh3)4 (2.5 g, 2.2 mmol) and heated to reflux overnight. The reaction mixture was concentrated and the resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil. LRMS m/z (M+H) 160.2 found, 160.1 required.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting material was purified directly by gradient elution on silica gel (0 to 20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f04b5d81594a413e92f9357bcf13a903
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273033B2

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