Sodium Hydroxide → 2-n-Butyl-3-[4-(N-t-butyl-3-azetidinoxy)benzoyl]benzofuran

HRID 1577014Notes

Reaction equation

HRID 1577014 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[C:23]([N:27]1[CH2:30][CH:29](Cl)[CH2:28]1)([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:29]2[CH2:30][N:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:28]2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 96670(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketoneHCID 109971861-(Tert-butyl)-3-chloroazetidine

Product 1

HCID 215105062-n-Butyl-3-[4-(N-t-butyl-3-azetidinoxy)benzoyl]benzofuran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.98 g. (13.5 mmol.) of 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran, 2.0 g. (13.5 mmol.) of N-t-butyl-3-chloroazetidine and 0.54 g. of sodium hydroxide in 75 ml. of ethanol was refluxed for five hours. The reaction mixture was cooled, filtered and 125 ml. of 10% aqueous sodium hydroxide solution was added. The mixture was extracted three times with chloroform, the combined extracts were evaporated to dryness and the residue was chromatographed on alumina with chloroform as eluant to give the title compound.

Workup

  1. additionA mixture of 3.98 g
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. additionof 10% aqueous sodium hydroxide solution was added
  5. extractionThe mixture was extracted three times with chloroform
  6. customthe combined extracts were evaporated to dryness
  7. customthe residue was chromatographed on alumina with chloroform as eluant

Sources & evidence

ORD record
ord-ef9d1bc1a75f481eaf7729a0fb778372
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

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