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

HRID 2110847Notes

Reaction equation

HRID 2110847 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.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 82844Platinum oxide (PtO)CatalystHCID 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 oxide (300 mg) was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title compound (5.97 g, yield 84%) as a colorless oil. 1H NMR (CDCl3) δ: 1.23 (3H, t, J=7.2 Hz), 2.58 (2H, t, J=7.6 Hz), 2.90 (2H, t, J=7.6 Hz), 3.77 (3H, s), 4.12 (2H, q, J=7.2 Hz), 6.57-6.63 (2H, m), 7.07-7.13 (1H, m).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ec8d4e000aea49779568c814c67469f6
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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