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

HRID 1899098ノート

反応式

HRID 1899098 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-34813a3ebbfc4ae1907da738b66c1d2e
出典データセット
uspto-grants-1996_11
特許番号
US05571810

反応ノート

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