Potassium Carbonate → 2-{2-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrrole

HRID 2286519Notes

Reaction equation

HRID 2286519 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[CH:11][CH:12]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 13725072HCID 13725072, compound

Product 1

HCID 137555112-{2-[(Oxiran-2-yl)methoxy]phenyl}-1H-pyrroleYield 48.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.0 g of 2-(o-hydroxyphenyl)-pyrrole, 7.3 g of epibromohydrin and 11.4 g of dry potassium carbonate in 50 ml of acetone are refluxed for 7 hours. After the mixture has cooled, it is filtered and the filter residue is washed with acetone. The combined filtrates are freed from the solvent by distillation. The residue is chromatographed twice on silica gel, using methylene chloride as the eluant, and gives 4.6 g (48% of theory) of 2-[2-(2,3-epoxypropoxy)-phenyl]-pyrrole as a colorless oil.

Workup

  1. temperatureAfter the mixture has cooled
  2. filtrationit is filtered
  3. washthe filter residue is washed with acetone
  4. distillationThe combined filtrates are freed from the solvent by distillation
  5. customThe residue is chromatographed twice on silica gel

Sources & evidence

ORD record
ord-98589bb4cfab4190b560fbd322e493b6
Source dataset
uspto-grants-1981_05
Patent number
US04267187

Reaction notes

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