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

HRID 1710160Notes

Reaction equation

HRID 1710160 reaction equation
[CH:1]1[C:2]2[CH:19]=[CH:18][C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:10]=[CH:9][C:8]=3[C:3]=2[O:4][C:5]=1[CH2:6][OH:7].[Mn]([O-])([O-])(=O)=O.[Ba+2]>C(Cl)Cl>[CH:1]1[C:2]2[CH:19]=[CH:18][C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:10]=[CH:9][C:8]=3[C:3]=2[O:4][C:5]=1[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 3084030Barium manganateHCID 14770239Phenanthro[1,2-b]furan-2-methanol

Product 1

HCID 14770240Phenanthro[1,2-b]furan-2-carbaldehydeYield 91%

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 phenanthro[1,2-b]furan-2-methanol (14A, 5.84 g, 23.5 mmol), barium manganate (Aldrich, 12.06 g, 47 mmol) and dry CH2Cl2 (400 mL). The mixture was refluxed for 6 h, filtered and the resulting dark yellow solution filtered through a small plus of SiO2 to remove inorganic salts and polar baseline material. The solvent was then removed by rotary evaporation and the crude material recrystallized using CH2Cl2 /hexane to give after drying 5.17 g (91% yield) of phenanthro[1,2-b]furan-2-carbaldehyde, mp 169°, (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 plus of SiO2
  6. customto remove inorganic salts and polar baseline material
  7. customThe solvent was then removed by rotary evaporation
  8. customthe crude material recrystallized
  9. customto give

Sources & evidence

ORD record
ord-bd2242abc97b4a64bebbd2c0aea28bb0
Source dataset
uspto-grants-1990_08
Patent number
US04952597

Reaction notes

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