Water → 3-Methyl-3-(4-chlorophenyl)-1-trimethylstannyl-1-butene

HRID 54271

Reaktionsgleichung

Reaktionsgleichung von HRID 54271
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)([CH3:6])[CH:3]=[CH:4]I.C([Li])CCC.[CH3:19][Sn:20](Cl)([CH3:22])[CH3:21].O>O1CCCC1>[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)([CH3:6])[CH:3]=[CH:4][Sn:20]([CH3:22])([CH3:21])[CH3:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 542638883-Methyl-3-(4-chlorophenyl)-1-iodo-1-buteneHCID 178418339Butyllithium

Produkt 1

HCID 676329003-Methyl-3-(4-chlorophenyl)-1-trimethylstannyl-1-buteneAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-90 °C

Versuchsvorschrift

A stirring solution of 4.8 grams (0.016 mole) of 3-methyl-3-(4-chlorophenyl)-1-iodo-1-butene in 50 mL of tetrahydrofuran is cooled to about -90° C., and 6.9 mL (0.01 8 mole) of n-butyllithium (2.5M in hexane) is added dropwise at a rate to maintain the reaction mixture temperature at about -85° to -90° C. Upon completion of the addition, the reaction mixture is stirred at -90° C. for 30 minutes. After this time, a solution of 3.7 grams (0.019 mole) of trimethyltin chloride in 10 mL of tetrahydrofuran is added dropwise at a rate sufficient to maintain the reaction mixture temperature at about -85° to -90° C. Upon completion of addition, the reaction mixture is again stirred at -90° C. for 30 minutes. After this time, the reaction mixture is allowed to warm to ambient temperature where it is stirred for about 18 hours. The reaction mixture is then poured into 150 mL of water and extracted with 150 mL of diethyl ether. The ether extract is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 4.8 grams of 3-methyl-3-(4-chlorophenyl)-1-trimethylstannyl-1-butene. The NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. temperatureto maintain the reaction mixture temperature at about -85° to -90° C
  2. additionUpon completion of the addition
  3. temperatureto maintain the reaction mixture temperature at about -85° to -90° C
  4. additionUpon completion of addition
  5. stirringthe reaction mixture is again stirred at -90° C. for 30 minutes
  6. temperatureto warm to ambient temperature where it
  7. stirringis stirred for about 18 hours
  8. extractionextracted with 150 mL of diethyl ether
  9. extractionThe ether extract
  10. dry with materialis dried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5265c609d750480b8b3ec7e1eb63a113
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622954

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