2-Propenoic acid, 3-(2-naphthalenyl)-, ethyl ester → Ethyl 3-(naphthalen-2-yl)propanoate

HRID 743393Notes

Reaction equation

HRID 743393 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[H][H]>C(O)C.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 44543982-Propenoic acid, 3-(2-naphthalenyl)-, ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 14022513Ethyl 3-(naphthalen-2-yl)propanoateYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4.29 g of this ethyl 3-(2-naphthyl)-2-propenoate were dissolved in 60 ml of ethanol. The solution was stirred at room temperature for 3 hours in an atmosphere of hydrogen at atmospheric pressure and in the presence of 500 mg of 5% w/w palladium-on-charcoal. At the end of this time, the catalyst was removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.04 g (yield 93%) of ethyl 3-(2-naphthyl)propionate as a colorless oil.

Workup

  1. customAt the end of this time, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-29201eafb8e648c2811f248070c8ba55
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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