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

HRID 728610Notes

Reaction equation

HRID 728610 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 14770240Phenanthro[1,2-b]furan-2-carbaldehydeYield 134.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-937a8bc3f7744cb58b1766da1b607321
Source dataset
uspto-grants-1991_09
Patent number
US05049581

Reaction notes

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