2-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolane → 2-[4-(2-Ethoxycarbonylethyl)naphthyl]dioxolane

HRID 1166743Notes

Reaction equation

HRID 1166743 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:22][CH2:21][CH2:20][O:19]2)=[CH:10][CH:9]=1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:19][CH2:20][CH2:21][O:22]2)=[CH:10][CH:9]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 536829332-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolane

Product 1

HCID 545306942-[4-(2-Ethoxycarbonylethyl)naphthyl]dioxolaneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[4-(2-ethoxycarbonylvinyl)naphthyl]dioxolane (701 mg, 2.35 mmol) in ethyl acetate (15 mL) was added palladium (5% on BaCO3, 51 mg). The mixture was stirred under a hydrogen atmosphere for 16 hr, filtered by suction through Celite and concentrated to provide 689 mg (98%) of a colorless oil.

Workup

  1. filtrationfiltered by suction through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f176542c60f46da9c62d93a4287629c
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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