Chloroform → HCID 54142217, compound

HRID 2295150Notes

Reaction equation

HRID 2295150 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:25][CH:24]=2)=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)[Cl:36].ClN1C(=O)CCC1=O>C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:27][CH:28]=2)=[C:16]([Cl:36])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 53730416HCID 53730416, compound

Product 1

HCID 54142217HCID 54142217, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy) phenyl)-2-phenyl ethylene (3.5 g, 7.5 mmol) and chloroform 935 mL). Add N-chlorosuccinimide (1.99 g, 14.9 mmol). Heat a t reflux. After 18 hours, cool the reaction mixture and extract with water, aqueous saturated sodium bicarbonate solution and water. Dry the organic layer over MgSO4, filter, and dry in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane to give 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy)phenyl)-2-chloro-2-phenyl ethylene.

Workup

  1. temperatureHeat a t
  2. temperaturereflux
  3. temperaturecool the reaction mixture
  4. extractionextract with water, aqueous saturated sodium bicarbonate solution and water
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customdry in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-0be34da8350e43338f7ea6810fba24c8
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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