Barium manganate → Phenanthro[1,2-b]furan-2-carbaldehyde

HRID 1073632

Reaktionsgleichung

Reaktionsgleichung von HRID 1073632
[O:1]1[C:5]([CH2:6][OH:7])=[CH:4][C:3]2[CH:8]=[CH:9][C:10]3[C:15]([C:2]1=2)=[CH:14][CH:13]=[CH:12][CH:11]=3.[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[CH:4]1[C:3]2[CH:8]=[CH:9][C:10]3[C:11]4[CH:4]=[CH:3][CH:2]=[CH:15][C:12]=4[CH:13]=[CH:14][C:15]=3[C:2]=2[O:1][C:5]=1[CH:6]=[O:7]

Komponenten

4

Edukt 2

HCID 3084030Barium manganateHCID 14555902Naphtho[1,2-b]furan-2-methanol

Produkt 1

HCID 14770240Phenanthro[1,2-b]furan-2-carbaldehydeAusbeute 134,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a RB flask equipped with magnetic stirring bar, reflux condenser, N2 inlet line with bubbler was added naphtho[1,2-b]furan-2-methanol (11A, 4.8 g, 24.2 mmol), barium manganate (Aldrich, 12.4 g, 48 mmol) and dry CH2Cl2 (500 mL). The mixture was refluxed for 6 h, filtered and the resulting dark yellow solution filtered through a small plug of SiO2 to remove inorganic salts and polar materials. The solvent was then removed by rotary evaporation and the crude material recrystallized using CH2Cl2 /pentane to give after drying 4.02 g (84.7% yield) of phenanthro[1,2-b]furan-2-carbaldehyde, mp 123°, (C,H).

Aufarbeitung

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser, N2 inlet line with bubbler
  3. temperatureThe mixture was refluxed for 6 h
  4. filtrationfiltered
  5. filtrationthe resulting dark yellow solution filtered through a small plug of SiO2
  6. customto remove inorganic salts and polar materials
  7. customThe solvent was then removed by rotary evaporation
  8. customthe crude material recrystallized
  9. customto give

Quellen und Nachweise

ORD-Eintrag
ord-1b312e05699648f99130d05cacdcd692
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04970227

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