Acetic Acid → 1-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one

HRID 908192ノート

反応式

HRID 908192 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([N+]([O-])=O)[CH3:13])=[CH:7][C:6]=1[C:17]([F:20])([F:19])[F:18])(=[O:4])=[O:3].C(O)(=[O:23])C>[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:23])[CH3:13])=[CH:7][C:6]=1[C:17]([F:20])([F:19])[F:18])(=[O:4])=[O:3]

参加物

4

反応物 2

HCID 176Acetic Acid2 回HCID 673913281-Methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene

生成物 1

HCID 673910181-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one

試薬・触媒・溶媒 1

HCID 23925Iron触媒

反応条件

温度
100 °C

実験手順

A solution of freshly prepared 1-methanesulfonyl-4-(2-nitro-propenyl)-2-trifluoromethyl-benzene (59b) (14 g, 45 mmol) in acetic acid (100 ml) is added slowly to a stirred slurry of Iron powder (27.6 g, 495 mmol) in acetic acid (100 ml) at 60° C. The reaction is then stirred at 100° C. for 2 hours then allowed to cool and poured onto ice-water (300 ml). After filtration through celite, washing with dichloromethane (500 ml), the organic extract is separated and washed with water (3×300 ml) followed by brine (500 ml). The organic extract is dried (MgSO4) and concentrated to give a red oil. Chromatography on silica, eluting with ethyl acetate-hexane, affords the titled compound as a white solid.

後処理

  1. temperatureto cool
  2. additionpoured onto ice-water (300 ml)
  3. filtrationAfter filtration through celite
  4. washwashing with dichloromethane (500 ml)
  5. extractionthe organic extract
  6. customis separated
  7. washwashed with water (3×300 ml)
  8. extractionThe organic extract
  9. dry with materialis dried (MgSO4)
  10. concentrationconcentrated
  11. customto give a red oil
  12. washChromatography on silica, eluting with ethyl acetate-hexane

出典と根拠

ORDレコード
ord-67282e44503a458fa14bfe8f0055b058
出典データセット
uspto-grants-2011_09
特許番号
US08017608B2

反応ノート

読み込み中…