HCID 58629899, compound → Ethyl 3-(3-fluoro-4-hydroxyphenyl)propionate

HRID 1391780Notes

Reaction equation

HRID 1391780 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>[Pd].CCO>[F:1][C:2]1[CH:3]=[C:4]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 58629899HCID 58629899, compound

Product 1

HCID 3023769Ethyl 3-(3-fluoro-4-hydroxyphenyl)propionateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (2E)-3-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-2-propenoate (205 mg, 0.68 mmol) and 10% Pd/C catalyst (40 mg) in EtOH (4 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 16.5 h. The mixture was then filtered through celite placed directly on the top of a SPE (silica, 5 g cartridge) eluting with EtOH. The filtrate was reduced under vacuum and the residue purified further by SPE (silica, 5 g cartridge) eluting with cyclohexane:EtOAc (gradient 25:1 to 3:1) to afford the title compound (140 mg).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washeluting with EtOH
  3. customthe residue purified further by SPE (silica, 5 g cartridge)
  4. washeluting with cyclohexane

Sources & evidence

ORD record
ord-1d302b1366b349af968766b81649ebb6
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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