2-(2-(4-(2,3-Difluoro-4-ethoxyphenyl)cyclohexylidene)-ethyl)-1,3-dioxane → HCID 178466566, compound

HRID 2120502Notes

Reaction equation

HRID 2120502 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][C:15](=[CH:18][CH2:19][CH:20]2[O:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:14][CH2:13]1>C1(C)C=CC=CC=1.C(O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][CH:20]2[O:21][CH2:22][CH2:23][CH2:24][O:25]2)[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 220205192-(2-(4-(2,3-Difluoro-4-ethoxyphenyl)cyclohexylidene)-ethyl)-1,3-dioxane

Product 1

HCID 178466566HCID 178466566, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21863594Toluene ethanolSolvent

Procedure

The 2-(2-(4-(2,3-difluoro-4-ethoxyphenyl)cyclohexylidene)-ethyl)-1,3-dioxane (36.9 mmol) obtained by the reaction of Step 3 was dissolved in 100 ml of a mixed solvent of toluene/ethanol (1/1), 4.0 g of 5-wt %-palladium/carbon catalyst was added, and the solution was stirred for 7 hours at room temperature under a hydrogen pressure of 1-2 kg/cm2. After the catalyst was filtered off, the solvent was distilled off from the filtrate under reduced pressure, the residue was subjected to silica gel column chromatography (eluent: a mixed solvent of ethyl acetate/toluene=3/7), the solvent was distilled off under reduced pressure, and the product was re-crystallized from ethanol to form 2-(2-(trans-4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexyl)-ethyl)-1,3-dioxane (36.9 mmol).

Workup

  1. additionwas added
  2. filtrationAfter the catalyst was filtered off
  3. distillationthe solvent was distilled off from the filtrate under reduced pressure
  4. distillationa mixed solvent of ethyl acetate/toluene=3/7), the solvent was distilled off under reduced pressure
  5. customthe product was re-crystallized from ethanol

Sources & evidence

ORD record
ord-999d441aa631417fb021d908d1812ea9
Source dataset
uspto-grants-2004_02
Patent number
US06692657B1

Reaction notes

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