Tributylvinyltin → HCID 86675861, Verbindung

HRID 1427766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427766
Br[C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:11]([C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)=[CH2:12]

Komponenten

5

Edukt 2

HCID 81998Tributylvinyltin2×HCID 2734889(1R)-1-(3-bromophenyl)ethan-1-ol

Produkt 1

HCID 86675861HCID 86675861, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysator2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Bis(triphenylphosphine)palladium(II) dichloride (360 mg, 0.512 mmol) was added to a degassed solution of (R)-1-(3-bromo-phenyl)-ethanol (1.03 g, 5.123 mmol) and tributyl(vinyl)tin (1.8 ml, 6.15 mmol) in toluene (10 ml) under N2 and the reaction was stirred at 45° C. for 18 h. Tributyl(vinyl)tin (2.56 mmol, 750 uL) and bis(triphenylphosphine)palladium(II) dichloride (0.256 mmol, 180 mg) were added and stirring was continued for 18 h. The reaction was cooled and the solvent evaporated to afford a residue which was absorbed onto SiO2. Purification by SiO2 (3:11-hexane/ethyl acetate) afforded 13a as a yellow oil (675 mg, 89%). 1H NMR (300 MHz, CDCl3) δ7.49 (1H, s), 7.33 (3H, m), 6.75 (1H, dd, J=17.6, 10.9 Hz), 5.80 (1H, d, J=17.6 Hz), 5.28 (1H, d, J=10.7 Hz), 4.93 (1H, m), 1.81 (1H, d, J=3.1 Hz), 1.52 (3H, d, J=6.5 Hz).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 18 h
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated
  5. customto afford a residue which
  6. customwas absorbed onto SiO2
  7. customPurification by SiO2 (3:11-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2473b59140e249b0913a7089a4a6b8dd
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933015B2

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