2-{1-[2-(Benzyloxy)phenyl]vinyl}-6-phenylpyridine → 2-{1-[2-(Benzyloxy)phenyl]ethyl}-6-phenylpyridine

HRID 1037664Notes

Reaction equation

HRID 1037664 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[CH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 671047992-{1-[2-(Benzyloxy)phenyl]vinyl}-6-phenylpyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 671052982-{1-[2-(Benzyloxy)phenyl]ethyl}-6-phenylpyridineYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 18.0 g (50.0 mmol) of 19, 1.8 g of 10% Pd on charcoal, and 180 mL of anhydrous ethanol was hydrogenated in a stainless steel autoclave at 20 atm constant pressure of hydrogen and 80° C. The reaction was carried out for ca. 4 hr, i.e. until hydrogen consumption was finished. The resulting mixture was filtered through glass frit, and the filtrate was evaporated to dryness. The product was isolated from the residue using flash-chromatography on silica gel 60 (40-63 um, eluent: hexanes-ethyl acetate from 50:1 to 2:1, vol.) to yield 13.1 g (73%) of the title product.

Workup

  1. customi.e. until hydrogen consumption
  2. filtrationThe resulting mixture was filtered through glass frit
  3. customthe filtrate was evaporated to dryness
  4. customThe product was isolated from the residue

Sources & evidence

ORD record
ord-f138548bc87c491197cefd17ba2842f5
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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