Diethyl Ether → HCID 14570897, compound

HRID 1607263Notes

Reaction equation

HRID 1607263 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, 3.5mmoles) 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, 1mmole) 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 agueous 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 agueous 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-ea30b32eea15407c8d2b03482957c1a8
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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