2-(4-Ethoxy-2,3-difluorophenyl)-5-propenylselenophene → HCID 59456299, compound

HRID 1873400Notes

Reaction equation

HRID 1873400 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][CH3:17])=[CH:13][CH:14]=2)=[C:6]([F:18])[C:5]=1[F:19])[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][CH3:17])=[CH:13][CH:14]=2)=[C:6]([F:18])[C:5]=1[F:19])[CH3:2]

Participants

4

Reactant 1

HCID 722902422-(4-Ethoxy-2,3-difluorophenyl)-5-propenylselenophene

Product 1

HCID 59456299HCID 59456299, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.65 g (11.0 mmol) of 2-(4-ethoxy-2,3-difluorophenyl)-5-propenylselenophene are hydrogenated in 35 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, and the crude product is purified by column chromatography (SiO2, n-heptane:EtOAc=4:1→2:1). The further purification is carried out by recrystallisation from n-heptane. 2-(4-Ethoxy-2,3-difluorophenyl)-5-propylselenophene is obtained as a colourless solid (m.p. 64° C.).

Workup

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

Sources & evidence

ORD record
ord-1115d22705ae44469de78ee79b70a61e
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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