E-1-[4-(2-benzyloxyethoxy)phenyl]-4-chloro-1,2-diphenyl-but-1-ene → E-Ospemifene

HRID 1937657Notes

Reaction equation

HRID 1937657 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:19](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)\[CH2:20][CH2:21][Cl:22])=[CH:14][CH:13]=1)C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:22][CH2:21][CH2:20]/[C:19](/[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[C:18](\[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:17][CH:16]=1)/[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 1

HCID 22461339E-1-[4-(2-benzyloxyethoxy)phenyl]-4-chloro-1,2-diphenyl-but-1-ene

Product 1

HCID 9842777E-Ospemifene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.9 g of E-1-[4-(2-benzyloxyethoxy)phenyl]-4-chloro-1,2-diphenyl-but-1-ene was dissolved in the mixture of ethyl acetate (60 ml) and ethanol (60 ml). Palladium on carbon (5%, 0.7 g) was added and the solution was stirred vigorously under a hydrogen atmosphere at room temperature until there was not any starting compound left (thin layer chromatography). Palladium on carbon was filtered off through siliceous earth and the filtrate was evaporated to dryness. The residue was crystallized several times from the mixture of ethanol and water.

Workup

  1. waitleft (thin layer chromatography)
  2. filtrationPalladium on carbon was filtered off through siliceous earth
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was crystallized several times
  5. additionfrom the mixture of ethanol and water

Sources & evidence

ORD record
ord-966dce5f36d1459caba8db78bd7a0bc2
Source dataset
uspto-grants-2002_05
Patent number
US06395785B1

Reaction notes

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