2,2'-Bipyridine → HCID 58755280, compound

HRID 1163313Notes

Reaction equation

HRID 1163313 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH2:17][CH2:16]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1C1C=CC=CN=1>O1CCOCC1.[Pd]>[O:1]([C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18][CH2:17][CH2:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14742,2'-BipyridineHCID 58755276HCID 58755276, compound

Product 1

HCID 58755280HCID 58755280, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl (6-((3-phenoxybenzyl)oxy)-3,4-dihydro-1-naphthalenyl)acetate (1.04 g, 2.51 mmol) and 2,2′-bipyridyl (0.197 g, 1.26 mmol) in 1,4-dioxane (10 mL) was added 10% palladium on carbon (50%, water wet, 0.2 g), and the mixture was stirred under hydrogen atmosphere (balloon pressure) at room temperature for 24 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-30% ethyl acetate/hexane) to give the title compound (0.481 g, yield 46%) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1536abd1ae604968abe573c0e5d76fd2
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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