Toluene → 3-{5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}-2-butenenitrile

HRID 1899098Notes

Reaction equation

HRID 1899098 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:5]=1)(=O)[CH3:2].C1(P(=C[C:46]#[N:47])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1(C)C=CC=CC=1>>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[S:8][C:4]([C:1]([CH3:48])=[CH:2][C:46]#[N:47])=[CH:5][C:6]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 106431405-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene

Product 1

HCID 539504123-{5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}-2-butenenitrile

Procedure

A mixture of 5-acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1.8 g) and (triphenylphosphoranylidene)acetonitrile (3.2 g) in toluene (40 ml) was refluxed for 28 hours. The mixture was cooled and filtered. The filtrate was concentrated and the residue (4.2 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (10:1). The obtained crystals (1.8 g) were recrystallized from ethanol to give colorless crystals of 3-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}-2-butenenitrile (1.5 g).

Workup

  1. temperaturewas refluxed for 28 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue (4.2 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (10:1)
  6. customThe obtained crystals (1.8 g) were recrystallized from ethanol

Sources & evidence

ORD record
ord-34813a3ebbfc4ae1907da738b66c1d2e
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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