Tetrabutylammonium Fluoride → beta-Methylenephenethyl alcohol

HRID 77326

Reaktionsgleichung

Reaktionsgleichung von HRID 77326
C([Si](C)(C)[O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:10]1([C:8](=[CH2:9])[CH2:7][OH:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67155247tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

Produkt 1

HCID 80106beta-Methylenephenethyl alcoholAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a well stirred solution of tert-butyl-dimethyl-(2-phenyl-allyloxy)-silane (1.3 g, 5.23 mmol) in tetrahydrofuran (10 mL) is slowly added a solution of a 1 N tetrabutylammonium fluoride in tetrahydrofuran (10.5 mL, 10.5 mmol). The reaction is allowed to stir for 20 min, quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield 700 mg of the title compound.

Aufarbeitung

  1. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted several times with ethyl acetate The organic layers
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified via silica gel chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-040cf4c5b67048c3a151c517cf90500a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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