Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]- → HCID 21898100, Verbindung

HRID 2099145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099145
[CH2:1]([Li])CCC.[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([Si:10]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:1])=[CH2:19])=[CH:14][CH:13]=1)([CH3:22])[CH3:21])([CH3:9])([CH3:8])[CH3:7]

Komponenten

5

Edukt 2

HCID 10857908Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-HCID 178418339Butyllithium

Produkt 1

HCID 21898100HCID 21898100, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl(triphenylphosphonium) bromide (17.1 g, 48.0 mmol) was suspended in THF (96 mL) and cooled to 0° C. n-Butyllithium (2.5 M in hexane, 19.2 mL, 48.0 mmol) was added dropwise to the mixture. The red solution was stirred at rt for 0.5 h. 1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethanone (10.0 g, 40.0 mmol) was added. The solution turned bright yellow and a white precipitate formed. The mixture was stirred for 1 h at rt and then the solution was quenched with saturated NaHCO3. The aqueous phase was extracted with diethyl ether and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, filtered and concentrated. The resultant mixture was eluted through a plug of silica gel (hexanes) and the filtrate was concentrated to provide tert-butyl-(4-isopropenyl-phenoxy)-dimethyl-silane (8.36 g, 84%) as a colorless oil. ESI MS (m/z 249, M+H).

Aufarbeitung

  1. additionwas added dropwise to the mixture
  2. customa white precipitate formed
  3. stirringThe mixture was stirred for 1 h at rt
  4. customthe solution was quenched with saturated NaHCO3
  5. extractionThe aqueous phase was extracted with diethyl ether
  6. washthe combined organic layers were washed with saturated NaHCO3
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe resultant mixture was eluted through a plug of silica gel (hexanes)
  11. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bafcb8acfc31476e80bb38bca7a4a33d
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569568B2

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