Diethyl Ether → HCID 14570897, compound

HRID 1534230Notes

Reaction equation

HRID 1534230 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][O:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][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:15][CH:14]=1.CC[O:37]CC>>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([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])=[O:37])=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 128132L 656224HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 14570897HCID 14570897, compoundYield 87%

Procedure

To an ice cold suspension of aluminium chloride (467 mg, 3.5 mmoles) in ether (100 mL) was added slowly lithium aluminium hydride (570 mg, 15 mmoles). After stirring for a period of 10 minutes, 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (491 mg, 1 mmole) in ether (10 mL) was added over a period of 2 minutes. The reaction mixture was stirred at room temperature for 10 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 and eluted with 10% ethyl acetate in hexane to yield 0.30 gm (87%) of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran, mp. 103°-105° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 10 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. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8309514962fd4d11a24a90b936484a1e
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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