Tetrabutylammonium Fluoride → [3-(Cyclopentylsulfanyl)phenyl]methanol

HRID 503095

Reaktionsgleichung

Reaktionsgleichung von HRID 503095
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([S:34][CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:29]=1)(C)C)(C)(C)C>C1COCC1>[CH:35]1([S:34][C:30]2[CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=[CH:32][CH:31]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 66845801Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane

Produkt 1

HCID 66347770[3-(Cyclopentylsulfanyl)phenyl]methanolAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of tetrabutylammonium fluoride in THF (1M, 6 ml) was added to a solution of tert-butyl{[3-(cyclopentylthio)benzyl]oxy}dimethylsilane (1.09 g) in dry THF (10 ml). The solution was stirred for 18 h under nitrogen and the solvent was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic phase was separated and washed with water. The organic phase was separated and the solvent evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane to give the title compound (0.65 g). LCMS RT=3.3 min

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between dichloromethane and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. customThe organic phase was separated
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with a stepped gradient of 10% to 100% dichloromethane-cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-a1f2079fea3b4810a81ee2e023de351d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776895B2

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