2-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene → 2-Propyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene

HRID 1873390Notes

Reaction equation

HRID 1873390 reaction equation
[CH:1]([C:4]1[Se:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)=[CH:2][CH3:3]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:4]1[Se:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]3[CH2:16][CH2:17][CH:18]([CH2:21][CH2:22][CH3:23])[CH2:19][CH2:20]3)=[CH:13][CH:14]=2)=[CH:7][CH:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 722902572-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Product 1

HCID 594563272-Propyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (2.69 mmol) of 2-(propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene is hydrogenated in 10 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→n-heptane:EtOAc=20:1). The further purification is carried out by recrystallisation from n-heptane. 2-Propyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as a colourless solid.

Workup

  1. filtrationis filtered
  2. concentrationconcentrated to dryness
  3. customthe crude product is purified by column chromatography (SiO2, n-heptane→n-heptane:EtOAc=20:1)
  4. customThe further purification
  5. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-4fc58dd152f9460eb94b4289914cc068
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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