2-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene → 2-(4-Ethoxy-2,3-difluorophenyl)-5-pentylselenophene

HRID 1873404Notes

Reaction equation

HRID 1873404 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Se:11][C:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=2)=[C:6]([F:20])[C:5]=1[F:21])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[Se:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=2)=[C:6]([F:20])[C:5]=1[F:21])[CH3:2]

Participants

4

Reactant 1

HCID 722902592-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene

Product 1

HCID 594562712-(4-Ethoxy-2,3-difluorophenyl)-5-pentylselenophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.30 g (6.22 mmol) of 2-(4-ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene are hydrogenated in 25 ml of ethyl acetate, in the presence of Pd/C (5% of Pd) at atmospheric pressure and RT. The reaction soln. is filtered and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:EtOAc=5:1→2:1). The further purification is carried out by recrystallisation from n-heptane. 2-(4-Ethoxy-2,3-difluorophenyl)-5-pentylselenophene is obtained as a colourless solid (m.p. 66° C.).

Workup

  1. filtrationis filtered
  2. concentrationconcentrated to dryness
  3. customThe crude product is purified by column chromatography (SiO2, n-heptane:EtOAc=5:1→2:1)
  4. customThe further purification
  5. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-df8660ae540847d4af4095d822940b22
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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