Diethyl Ether → Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 1987830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987830
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-].CCOCC>C1COCC1>[Si:35]([O:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 108935701-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]benzene

Produkt 1

HCID 11230163Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-Ausbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (1 M THF, 44 mL, 44 mmol) was added to a 0° C. solution of 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (14 g, 40 mmol) in THF (400 mL). The reaction was stirred for 30 minutes, then poured into a mixture of saturated NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted twice with Et2O. The organics were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed (1:9 EtOAc/hexanes) to provide the product as a colorless oil (8.0 g, 85%).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted twice with Et2O
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (1:9 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ba6191afb576451498c86c9e182ba568
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553842B2

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