Hydrochloric Acid → Ethyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

HRID 30744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30744
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([O:27][CH2:28][CH3:29])(=[O:26])[C:17]1[CH:25]=[CH:24][C:22](O)=[C:19]([O:20][CH3:21])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][C:22]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:16]([O:27][CH2:28][CH3:29])=[O:26]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12038Ethyl vanillateHCID 67749Trifluoromethanesulfonic anhydride

Produkt 1

HCID 22171362Ethyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (0.94 mL) was added to an ice-cooled mixture of ethyl vanillate (1.0 g) and pyridine (0.45 mL) in methylene chloride (5 mL) with stirring. The mixture was stirred for 10 min, and poured into a mixture of 1 mol/L hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/10) to afford ethyl 3-methoxy-4-trifluoromethanesulfonyloxybenzoate (1.47 g).

Aufarbeitung

  1. temperaturecooled
  2. stirringThe mixture was stirred for 10 min
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-178c977206fe4786a5e3c897eb1be400
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423185B2

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