Ethanol → HCID 18405027, compound

HRID 1017793Notes

Reaction equation

HRID 1017793 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:17])[C:10]([CH3:16])([CH3:15])[CH2:11][C:12]([OH:14])=[O:13])=[C:4]([CH3:18])[CH:3]=1.C(N1C=CN=C1)(N1[CH:25]=[CH:24]N=C1)=O.C(O)C>O1CCCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:17])[C:10]([CH3:15])([CH3:16])[CH2:11][C:12]([O:14][CH2:24][CH3:25])=[O:13])=[C:4]([CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 18404861HCID 18404861, compound

Product 1

HCID 18405027HCID 18405027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.2 g (10 mmol) of 4-(4-bromo-2,5-dimethyl-phenyl)-3,3-dimethyl4-oxo-butanoic acid in tetrahydrofuran is combined with 3.60 g (11 mmol) of carbonyldiimidazole and stirred for 1 hour at ambient temperature. The solvent is replaced by 20 ml of ethanol and the mixture is heated to boiling for 2 hours. Then the solvent is distilled off, the crude product is taken up in methylene chloride, washed with water, dried with sodium sulphate, concentrated and purified by flash chromatography (silica gel; ethyl acetate/petroleum ether=3:97).

Workup

  1. temperaturethe mixture is heated
  2. waitto boiling for 2 hours
  3. distillationThen the solvent is distilled off
  4. washwashed with water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. custompurified by flash chromatography (silica gel; ethyl acetate/petroleum ether=3:97)

Sources & evidence

ORD record
ord-e6ba70411b844fc5943acb5f9de33a44
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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