Tetrahydrofuran → Ethyl 3-(2-Fluoro-4-methoxyphenyl)propanoate

HRID 732181Notes

Reaction equation

HRID 732181 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].O1CCCC1>[Pt](=O)=O.C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 59838333ethyl(2E)-3-(2-fluoro-4-methoxyphenyl)acrylate

Product 1

HCID 23083097Ethyl 3-(2-Fluoro-4-methoxyphenyl)propanoateYield 84%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (2E)-3-(2-fluoro-4-methoxyphenyl)acrylate (7.07 g, 31.5 mmol), tetrahydrofuran (50 mL), ethanol (5 mL) and platinum dioxide (300 mg) was stirred overnight under a hydrogen atmosphere at room temperature. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the title compound (5.97 g, yield 84%) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a04ae58b1b23453aa3a17c455df7a439
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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