Epichlorohydrin → HCID 73183747, compound

HRID 1906190Notes

Reaction equation

HRID 1906190 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>CC(C)=O>[O:29]1[CH2:28][CH:27]1[CH2:25][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH:11]=[CH:10][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7835Epichlorohydrin2×HCID 11430Potassium CarbonateHCID 54527042HCID 54527042, compound

Product 1

HCID 73183747HCID 73183747, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.8 g of the product of Step A, 120 ml of acetone, 3.6 g of potassium carbonate and 9.6 ml of epichlorhydrin was refluxed for 24 hours with stirring under an inert atmosphere. Then, 9.6 ml of epichlorhydrin were added and reflux was continued for 5 hours. After filtering, the solvent was evaporated under reduced pressure at 60° C., and the fractions with Rf=0.35 were recovered by chromatography on silica (eluent:methylene chloride) to obtain 5.25 g of 4-[2-[4-[(2-oxiranyl)-methoxy]-phenyl]-ethenyl]-1H-indole melting at ≃128° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturereflux
  3. filtrationAfter filtering
  4. customthe solvent was evaporated under reduced pressure at 60° C.
  5. customthe fractions with Rf=0.35 were recovered by chromatography on silica (eluent:methylene chloride)

Sources & evidence

ORD record
ord-2c9facddf2b1480db53320bec3e5f01f
Source dataset
uspto-grants-1987_03
Patent number
US04650811

Reaction notes

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