Silane, trimethyl((1-methylethenyl)oxy)- → (4R,5R)-2-allyl-2-isopropenyloxy-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3,2]dioxasilolane

HRID 493461

Reaktionsgleichung

Reaktionsgleichung von HRID 493461
[Li]C.C[Si](C)(C)[O:5][C:6]([CH3:8])=[CH2:7].[CH2:11]([Si:14]1(Cl)[O:18][C@@H:17]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:16]([C:24]([CH3:28])([O:26][CH3:27])[CH3:25])[O:15]1)[CH:12]=[CH2:13]>CCCCC>[CH2:11]([Si:14]1([O:5][C:6]([CH3:8])=[CH2:7])[O:18][C@@H:17]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:16]([C:24]([CH3:28])([O:26][CH3:27])[CH3:25])[O:15]1)[CH:12]=[CH2:13]

Komponenten

5

Edukt 3

HCID 74599Silane, trimethyl((1-methylethenyl)oxy)-HCID 57681726HCID 57681726, VerbindungHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 57681748(4R,5R)-2-allyl-2-isopropenyloxy-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3,2]dioxasilolaneAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8003PentaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) solution of MeLi (13.0 mL; 21 mmol; 1.6 M in Et2O) was added 2-(trimethylsilyloxy)propene (2.8 g; 21 mmol). The solution was stirred 30 minutes at 0° C., and then warmed to room temperature and was stirred for 1 hour. The mixture was recooled to 0° C., and (4R,5R)-2-allyl-2-chloro-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3,2]dioxasilolane (6.6 g; 21 mmol) was added. The mixture was warmed to room temperature and stirred for 2 hours. The solution was diluted with pentane (20 mL), and the mixture was then filtered through a pad of celite. The filtrate was concentrated, and the residue was distilled under reduced pressure to give 3.0 g (43%) of (4R,5R)-2-allyl-2-isopropenyloxy-4,5-bis-(1-methoxy-1-methyl-ethyl)-[1,3,2]dioxasilolane as a clear, colorless liquid.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringwas stirred for 1 hour
  3. customwas recooled to 0° C.
  4. temperatureThe mixture was warmed to room temperature
  5. stirringstirred for 2 hours
  6. filtrationthe mixture was then filtered through a pad of celite
  7. concentrationThe filtrate was concentrated
  8. distillationthe residue was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-395477f10ae54dd890ad556b2871b438
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534905B2

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