Aluminum(III) Chloride → HCID 14570895, compound

HRID 1534209Notes

Reaction equation

HRID 1534209 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:43]=[CH:42][C:15]([C:16]([C:18]2[O:19][C:20]3[C:27]([Cl:28])=[CH:26][C:25]([CH2:29][CH2:30][CH3:31])=[C:24]([O:32]C(=O)C4C=CC(Cl)=CC=4)[C:21]=3[C:22]=2[CH3:23])=O)=[CH:14][CH:13]=1>CCOCC>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][C:18]2[O:19][C:20]3[C:27]([Cl:28])=[CH:26][C:25]([CH2:29][CH2:30][CH3:31])=[C:24]([OH:32])[C:21]=3[C:22]=2[CH3:23])=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 14579767HCID 14579767, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14570895HCID 14570895, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cold suspension of aluminium chloride (2.1 gm, 16 mmoles) in ether (300 mL) was added slowly lithium aluminium hydride (2.6 gm, 68 mmoles). After stirring for a period of 10 minutes, 2-(p-chlorobenzoyl)-3-methyl-4-(p-chlorobenzoyloxy)-5-propyl-7-chlorobenzofuran (2.3 gm, 4.6 mmoles) in ether (10 mL) was added over a period of 2 minutes. The reaction mixture was stirred at room temperature for 15 minutes. It was cooled with an ice bath and ice was added slowly. When the vigorous reaction subsided, the organic layer was separated and the aqueous phase was extracted with ether. The organic phases were combined, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel. Elution with 15% ethylacetate in hexane yielded 0.30 gm (87%) of 2-(p-chlorobenzyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran, mp.76°-77° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  2. temperatureIt was cooled with an ice bath
  3. additionice was added slowly
  4. customWhen the vigorous reaction
  5. customthe organic layer was separated
  6. extractionthe aqueous phase was extracted with ether
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on silica gel
  11. washElution with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-6045ab4baff445faa62162e50c03f8cf
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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