1,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene → (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]propane

HRID 704908Notes

Reaction equation

HRID 704908 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1)=[CH:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:8]=1>[Rh].C(O)C>[F:32][C:2]([F:1])([F:31])[CH:3]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=1)[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 537269141,1,1-Trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene

Product 1

HCID 14517038(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]propane

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]prop-2-ene (6 g), rhodium on alumina (0.45 g - commercially available from the Aldrich Chemical Company Ltd, The old Brickyard, New Road, Gillingham, Dorset, England) and ethanol (130 cm3) was stirred under hydrogen at a pressure of 3.2 atmospheres for 8 hours. The catalyst was removed by filtration and the solvent evaporated under reduced pressure. The residual oil was purified by column chromatography on a silica gel support, eluted with n-hexane containing 30% by volume dichloromethane, to give (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-[3-(4-chlorophenoxy)-4-fluorobenzyloxy]propane.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated under reduced pressure
  3. customThe residual oil was purified by column chromatography on a silica gel support
  4. washeluted with n-hexane containing 30% by volume dichloromethane

Sources & evidence

ORD record
ord-546e8e1207a54db18c92fb302da13289
Source dataset
uspto-grants-1991_01
Patent number
US04988826

Reaction notes

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