[6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methanol → [6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methane

HRID 234791

Reaction equation

HRID 234791 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)O)=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[O:8][C:7]=2[CH:29]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCCC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH2:11][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[C:9]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[O:8][C:7]=2[CH:29]=1

Participants

4

Reactant 2

HCID 18925541[6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 18925542[6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methane

Reagents, catalysts & solvents 1

HCID 7668PropylbenzeneSolvent

Procedure

A solution of 400 mg (1.02 mmol) of [6-Methoxy-2-(4-methoxyphenyl)benzo[b]furan-3-yl][4-methoxyphenyl]methanol was dissolved in 10 mL of n-propylbenzene and 200 mg (5.25 mmol) of LiAlH4 was added. The reaction mixture was heated to reflux under a nitrogen atmoshere for 45 minutes. After sixteen hours, the reaction was quenched by the addition of 5 mL of water. To this suspension was added 3 mL of 15% (W/N) NaOH and an additional 3 mL of water. This suspension was filtered. The resulting filterate separated into two layers. The top (organic) layer was removed and evaporated to dryness. The crude product was chromatographed on silica eluted with 20% EtOAc in hexane. The final product was crystallized from ether. This yielded 100 mg of the title compound as a solid with a low melting point.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under a nitrogen atmoshere for 45 minutes
  3. waitAfter sixteen hours
  4. customthe reaction was quenched by the addition of 5 mL of water
  5. additionTo this suspension was added 3 mL of 15% (W/N) NaOH
  6. filtrationThis suspension was filtered
  7. customThe resulting filterate separated into two layers
  8. customThe top (organic) layer was removed
  9. customevaporated to dryness
  10. customThe crude product was chromatographed on silica
  11. washeluted with 20% EtOAc in hexane
  12. customThe final product was crystallized from ether

Sources & evidence

ORD record
ord-1ac47aafe99a43dc9e239f504839bdfe
Source dataset
uspto-grants-1997_01
Patent number
US05596106

Linked notes

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