Epichlorohydrin → HCID 57291601, compound

HRID 1382842Notes

Reaction equation

HRID 1382842 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:31])[CH:20]=[CH:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>CC(C)=O>[O:11]1[CH2:10][CH:9]1[CH2:7][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:31])[CH:20]=[CH:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 538459351-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)prop-2-en-1-one

Product 1

HCID 57291601HCID 57291601, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

First 3.46 g of potassium carbonate and then 10.5 ml of epichlorohydrin were added to a solution of 4 g of 1-[2-hydroxyphenyl]-3-(1H-indol-4-yl)-2-propen-1-one in 80 ml of acetone and the mixture was refluxed for 50 hours under an inert atmosphere and was filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica. Elution with a 95-5 dichloromethane-ethyl acetate mixture yielded 2.26 g of 1-[2-[(2-oxiranyl)-methoxy]-phenyl]-3-(1H-indol-4-yl)-2-propen-1-one.

Workup

  1. temperaturethe mixture was refluxed for 50 hours under an inert atmosphere
  2. filtrationwas filtered
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was chromatographed over silica
  5. washElution with a 95-5 dichloromethane-ethyl acetate mixture

Sources & evidence

ORD record
ord-ed79a7725fa1420984771c47c737d67f
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

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