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Cesium carbonate → Trifluoro-methanesulfonic acid 3-acetyl-5-hydroxy-phenyl ester

HRID 417041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 417041
[C:1]([C:4]1[CH:5]=[C:6]([O:18]S(C(F)(F)F)(=O)=O)[CH:7]=[C:8]([O:10][S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[C:1]([C:4]1[CH:9]=[C:8]([O:10][S:11]([C:14]([F:17])([F:15])[F:16])(=[O:13])=[O:12])[CH:7]=[C:6]([OH:18])[CH:5]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 59496833Trifluoro-methanesulfonic acid 3-acetyl-5-trifluoromethanesulfonyloxy-phenyl ester

Produkt 1

HCID 59833966Trifluoro-methanesulfonic acid 3-acetyl-5-hydroxy-phenyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Trifluoro-methanesulfonic acid 3-acetyl-5-trifluoromethanesulfonyloxy-phenyl ester (9.9 g) was dissolved in 1,2-dimethoxyethane (80 mL), followed by addition of cesium carbonate (11.6 g). The resulting suspension was stirred at 80° C. for 3 h and then quenched with saturated solution of ammonium chloride. The solution was then extracted with diethyl ether and combined etherate extracts were washed with brine, dried over anhydrous sodium sulfate, and filtered through a silica pad. The filtrate was concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to afford 3.5 g of the title compound (52% yield). HRMS calcd for C19H7O5S1F3 [M+H]+ 285.0039, observed 285.0039.

Aufarbeitung

  1. customquenched with saturated solution of ammonium chloride
  2. extractionThe solution was then extracted with diethyl ether
  3. washwere washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered through a silica pad
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-2d33793ae83049e9a01678e22d748a9d
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08088936B2

Notizen zur Reaktion

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