Triethylamine → Triisopropyl{[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane

HRID 2264285

Reaktionsgleichung

Reaktionsgleichung von HRID 2264285
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1.C(N(CC)CC)C.FC(F)(F)S(O[Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])(=O)=O.[Cl-].[NH4+]>ClCCl>[CH:31]([Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:16][C:13]1[CH2:12][CH2:11][CH:10]([C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:15][CH:14]=1)([CH3:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 574243624-(2,4,5-Trifluorophenyl)cyclohexanone

Produkt 1

HCID 67065786Triisopropyl{[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A three-neck flask (1 L) containing a stirred solution of 4-(2,4,5-trifluorophenyl)cyclohexanone (15.8 g) in dichloromethane (160 mL) under a nitrogen atmosphere was cooled to 0° C. and then treated with triethylamine (22 mL) followed by triisopropylsilyl trifluoromethanesulfonate (25.4 g) while maintaining the temperature below 5° C. The solution was stirred at 0° for 30 min and then allowed to rise to ambient temperature over a period of 0.5 h. It was then treated with saturated aqueous ammonium chloride solution. The organic layer was separated, dried over anhydrous magnesium sulfate and evaporated. The crude product was chromatographed (silica gel, 3% ether in hexane) to yield the title compound.

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 5° C
  2. waitto rise to ambient temperature over a period of 0.5 h
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe crude product was chromatographed (silica gel, 3% ether in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-73796fe077a94abb8e44de766e7bcc96
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855206B2

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