2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propylthiophene

HRID 1943517Notes

Reaction equation

HRID 1943517 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]([CH:20]=[CH:21][CH3:22])=[CH:18][CH:19]=3)=[C:11]([F:23])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]>C1COCC1.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]([CH2:20][CH2:21][CH3:22])=[CH:18][CH:19]=3)=[C:11]([F:23])[CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 670675042-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene

Product 1

HCID 581606972-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propylthiophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.10 g (8.73 mmol) of 2-(4′-ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene are hydrogenated in 100 ml of THF, in the presence of Pd/C (5% of Pd) at atmospheric pressure and room temperature. The reaction solution is evaporated to dryness, and the crude product is purified by column chromatography (SiO2, n-heptane:toluene=9:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-(4′-ethyl-3-fluorobiphenyl-4-yl)-5-propylthiophene as a colourless solid (m.p. 41° C.).

Workup

  1. customThe reaction solution is evaporated to dryness
  2. customthe crude product is purified by column chromatography (SiO2, n-heptane:toluene=9:1)
  3. customThe further purification
  4. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-6ec4011b422847238a075917d702818e
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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