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

HRID 1289920Notes

Reaction equation

HRID 1289920 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 70116950z-1-[4-(2-Benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene

Product 1

HCID 3036505Ospemifene

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Z-1-[4-(2-benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene (36 g, 0.08 mol) was dissolved in the mixture of ethyl acetate (350 ml) and ethanol (350 ml). Palladium on carbon (5%, 0.28 g) was added and the solution was flushed with hydrogen gas 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. The residue was crystallized from the mixture of ethanol (155 ml) and water (65 ml). Yield 20 g.

Workup

  1. customthe solution was flushed with hydrogen gas until there
  2. waitleft (thin layer chromatography)
  3. filtrationPalladium on carbon was filtered off through siliceous earth
  4. customthe filtrate was evaporated
  5. customThe residue was crystallized from the mixture of ethanol (155 ml) and water (65 ml)

Sources & evidence

ORD record
ord-3f26f31f308f4818b09a5efebb46ba46
Source dataset
uspto-grants-1998_05
Patent number
US05750576

Reaction notes

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