Water → (5,5-Dimethyl-1,3-hexadiynyl)tri-n-butylstannane

HRID 1975548

Reaktionsgleichung

Reaktionsgleichung von HRID 1975548
C([Mg]Br)C.[CH3:5][C:6]([CH3:12])([CH3:11])[C:7]#[C:8][C:9]#[CH:10].[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].O>CCOCC>[CH3:5][C:6]([CH3:12])([CH3:11])[C:7]#[C:8][C:9]#[C:10][Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 11423565t-Butyl-1,3-butadiyneHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 19100263(5,5-Dimethyl-1,3-hexadiynyl)tri-n-butylstannaneAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(5,5-dimethyl-1,3-hexadiynyl)tri-n-butylstannane was synthesized as follows a solution containing ethylmagnesium bromide (19.3 millimoles) and 5,5-dimethyl-1,3hexadiyne (19.3 millimoles) in 50 milliliters of ether was refluxed for 5 hours under nitrogen, then cooled to -78° C. To this solution, 18.6 millimoles of tri-n-butyltin chloride in 10 milliliters of ether was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. Water was added to form a two-phase mixture, the phases were separated, and the aqueous phase was washed with ether. The ether wash was combined with the organic phase from the initial phase separation, and evaporated under reduced pressure to yield a crude oil. Distillation in vacuo produced 2.92 grams of pure (5,5-dimethyl-1,3-hexadiynyl)tri-n-butylstannane.

Aufarbeitung

  1. custom(5,5-dimethyl-1,3-hexadiynyl)tri-n-butylstannane was synthesized
  2. temperaturewas refluxed for 5 hours under nitrogen
  3. temperatureto warm to room temperature
  4. customto form a two-phase mixture
  5. customthe phases were separated
  6. washthe aqueous phase was washed with ether
  7. washThe ether wash
  8. customwas combined with the organic phase from the initial phase separation
  9. customevaporated under reduced pressure
  10. customto yield a crude oil
  11. distillationDistillation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d0b42673f9040a9a73fcb9f5ab5eaeb
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05286901

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