{2-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol → 2-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furaldehyde

HRID 1876938

Reaktionsgleichung

Reaktionsgleichung von HRID 1876938
[CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH2:8][OH:9])[CH3:2]>C(OCC)C.O1CCCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2]

Komponenten

5

Edukt 1

HCID 23074480{2-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol

Produkt 1

HCID 230743552-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furaldehydeAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of {2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (2.7 g) and manganese dioxide (6.8 g) in diethyl ether (20 mL) and tetrahydrofuran (20 mL) was stirred overnight at 40° C. Manganese dioxide was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (5% ethyl acetate/hexane to 20% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (0.66 g, 24%) as a yellow solid.

Aufarbeitung

  1. filtrationManganese dioxide was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (5% ethyl acetate/hexane to 20% ethyl acetate/hexane)
  4. customcrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-702d166f9b8142d3b86b750a9e79e101
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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