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Cyclopentanethiol → Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilane

HRID 219053
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 219053
[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](I)[CH:11]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([SH:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>CN1CCCC1=O.C(N(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([Si:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:22][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:11]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 15510CyclopentanethiolHCID 66845200Tert-butyl[(3-iodobenzyl)oxy]dimethylsilane

Produkt 1

HCID 66845801Tert-butyl([3-(cyclopentylthio)benzyl]oxy}dimethylsilaneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8471
Triethylamine
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Tert-butyl[(3-iodobenzyl)oxy]dimethylsilane (WO9513095) (1.44 g) in dry 1-methyl-2-pyrrolidone (15 ml) and triethylamine (4 ml) was stirred at room temperature under nitrogen. 1-1′Bis(diphenylphosphino)ferrocene (110 mg) and tris(dibenzylideneacetone)dipalladium(0) (258 mg) were added and the mixture was stirred for 15 min. Cyclopentyl mercaptan (0.42 g) was then added, and the reaction mixture stirred at 60° C. for 2 h. The reaction mixture was cooled to room temperature, poured onto water and extracted with diethyl ether. The combined organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The residue was purified on a 50 g SPE, eluting with a stepped gradient of 10 to 100% dichloromethane-cyclohexane to give the title compound (1.09 g) LCMS RT=4.67 min

Aufarbeitung

  1. stirringthe reaction mixture stirred at 60° C. for 2 h
  2. additionpoured onto water
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified on a 50 g SPE
  7. washeluting with a stepped gradient of 10 to 100% dichloromethane-cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-e05832aa3012408b875354d4737b7f28
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198483B2

Notizen zur Reaktion

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