2-[2-(3-Fluorophenyl)vinyl]naphthalene → 2-[2-(3-Fluorophenyl)ethyl]naphthalene

HRID 1712194Notes

Reaction equation

HRID 1712194 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1>[Pd].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 686157232-[2-(3-Fluorophenyl)vinyl]naphthalene

Product 1

HCID 686168432-[2-(3-Fluorophenyl)ethyl]naphthaleneYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A 60 ml Solumix/toluene (1:1) solution of 11.54 g (46.48 mmol) of the above 2-[2-(3-fluorophenyl)vinyl]naphthalene was added with 0.58 g of 5%-Pd/C and then stirred for 20 hours in an H2-atmosphere. The 5%-Pd/C was filtrated away from the reaction solution, and then the filtrate was condensed under a reduced pressure. The obtained gray solid of 11.18 g was purified with silica gel chromatography using toluene as the eluent to obtain a white solid of 11.05 g, which was recrystallized with a mixed solvent of Solumix/heptane in a ratio of 2:1 to obtain 10.43 g of 2-[2-(3-fluorophenyl)ethyl]naphthalene as white crystals.

Workup

  1. filtrationThe 5%-Pd/C was filtrated away from the reaction solution
  2. customcondensed under a reduced pressure
  3. customThe obtained gray solid of 11.18 g was purified with silica gel chromatography
  4. customto obtain a white solid of 11.05 g, which
  5. customwas recrystallized with a mixed solvent of Solumix/heptane in a ratio of 2:1

Sources & evidence

ORD record
ord-2722f4d3217c46a58b4e1d666231dd90
Source dataset
uspto-grants-2010_09
Patent number
US07790915B2

Reaction notes

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