Iodine → (3,5-diphenylfuran-2-yl)-phenyl-methanone

HRID 1726380Notes

Reaction equation

HRID 1726380 reaction equation
[C:1]1([C+:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)O2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].II.[OH2:33].[OH2:34].O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O>[C:13]1([C:11]2[CH:10]=[C:9]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:33][C:12]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:34])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 61475Sodium Thiosulfate PentahydrateHCID 178420061HCID 178420061, compound

Product 1

HCID 12211761(3,5-diphenylfuran-2-yl)-phenyl-methanoneYield 39.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a mixture of benzaldehyde (2.6 ml, 25.58 mmol) and acetophenone (6 ml, 51.44 mmol) in anhydrous benzene (3 ml), was added boron trifluoride diethyl etherate (8 ml, 63.13 mmol) at RT. The mixture was heated at reflux for 2 h, cooled to RT, acetone was added (5 ml), and the resulting dark red solution was poured into ether (250 ml). A dark yellow precipitate formed, which was isolated and redissolved in acetone (30 ml), ether was added until the yellow solid was formed, isolated and dried to provide 2,4,6-triphenyl-pyranylium (3.87 g, 48%, mw=309). To a suspension of 2,4,6-triphenyl-pyranylium (3.86 g, 12.5 mmol) in acetone (50 ml), was added a solution of Na2CO3 (1.7 g, 16 mmol) in H2O (4.6 ml), and the mixture was stirred at RT for 2 h. To the reaction mixture, iodine (4.1 g, 16.1 mmol) was added, and the resulting mixture was stirred at RT overnight, then poured into a solution of sodium thiosulfate pentahydrate (40.0 g, 160 mmol) in water (250 ml), extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to provide (3,5-diphenylfuran-2-yl)-phenyl-methanone (intermediate XXVIa, 1.6 g, 19%) as a yellow solid.

Workup

  1. stirringthe resulting mixture was stirred at RT overnight
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationthe organic solution concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1% EtOAc in hexane)

Sources & evidence

ORD record
ord-f150fb3e3a294cd7ae7efbc9e99d54cc
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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