(4-Phenylfuran-3-yl)methanol → 4-Phenyl-3-furaldehyde

HRID 915672

Reaktionsgleichung

Reaktionsgleichung von HRID 915672
[C:1]1([C:7]2[C:8]([CH2:12][OH:13])=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([C:7]2[C:8]([CH:12]=[O:13])=[CH:9][O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 1

HCID 15037154(4-Phenylfuran-3-yl)methanol

Produkt 1

HCID 150371484-Phenyl-3-furaldehydeAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Prepare a solution of (4-phenylfuran-3-yl)methanol (2.3 g, 13.2 mmol) in methylene chloride (20 mL). Add N-methylmorpoline N-oxide (2.2 g, 18.5 mmol) and powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propyl ammonium perruthenate. Warm the mixture to room temperature and stir for an additional 3 hours. Filter the reaction mixture through Celite® and concentrate the filtrate. Perform flash chromatography on silica gel eluting with 10% diethyl ether/hexane to afford 1.36 g of 4-phenyl-3-formylfuran. 1H NMR (CDCl3) δ 10.01 (s, 1H), 8.15 (s, 1H), 7.60 (s, 1H), 7.35-7.54 (m, 5H).

Aufarbeitung

  1. temperatureWarm the mixture to room temperature
  2. filtrationFilter the reaction mixture through Celite®
  3. concentrationconcentrate the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-d01dd0173fa64666a2494a297d85a9a0
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

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