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

HRID 1899098노트

반응식

HRID 1899098 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-34813a3ebbfc4ae1907da738b66c1d2e
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571810

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