Chlorosuccinimide → Des-N,N-diethylethanaMine 4-HydroxycloMiphene

HRID 2292495Notes

Reaction equation

HRID 2292495 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Cl:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[Cl:22])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 5074675Phenol, 4-(1,2-diphenylethenyl)-

Product 1

HCID 4553080Des-N,N-diethylethanaMine 4-HydroxycloMiphene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Combine (E and Z)-1-[(4-hydroxy)phenyl]-1,2-diphenyl-ethylene [Cacchi et al, Tet. Lets. 25, 3137-3140 (1984)] (0.90 g, 3.31 mmol) and N-chlorosuccinimide (0.486 g, 3.64 mmol) in chloroform (20 mL). Heat to reflux and allow to stir at reflux for 48 hours. Evaporate in vacuo. Chromatograph on silica gel eluting with 20% ethyl acetate/hexane to give the title compound as a solid: mp; 127°-129° C.

Workup

  1. temperatureHeat
  2. temperatureto reflux
  3. temperatureat reflux for 48 hours
  4. customEvaporate in vacuo

Sources & evidence

ORD record
ord-5b8a016ac8c54a3ebe026d4090661c33
Source dataset
uspto-grants-1997_11
Patent number
US05684004

Reaction notes

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