(E)-2-(6-fluoro-1-indanylidene)acetamide → (Z)-2-(6-fluoro-1-indanylidene)acetamide

HRID 362879ノート

反応式

HRID 362879 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1>ClCCl.CO.[Hg]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]/[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 9837001(E)-2-(6-fluoro-1-indanylidene)acetamide

生成物 1

HCID 11116858(Z)-2-(6-fluoro-1-indanylidene)acetamide収率 37%

試薬・触媒・溶媒 2

HCID 23931Mercury触媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A solution of (E)-2-(6-fluoro-1-indanylidene)acetamide (20 g,104.6 mmol) in dichloromethane:methanol(3:1) (1000 ml) was irradiated by an Canrad-Hanovia quartz, mercury-vapor photochemical immersion lamp, 450 wattts (Ace Glass, 7825-35) for 0.5 h. The volatiles were removed by spin evaporation in vacuo to give a beige residue. This residue was chromatographed on Silica Gel 60 using a step gradient going from ethyl acetate: hexanes(1:1) to ethyl acetate:ethanol(1:1). Fractions containing (Z)-2-(6-fluoro-1-indanylidene)acetamide were combined and concentrated by spin evaporation in vacuo. The resulting solid was slurried in hexanes to give 7.2 g (37%) of (Z)-2-(6-fluoro-1-indanylidene)acetamide as a white crystalline solid, m.p.,175°-177 ° C.;

後処理

  1. customThe volatiles were removed by spin evaporation in vacuo
  2. customto give a beige residue
  3. customThis residue was chromatographed on Silica Gel 60 using a step gradient
  4. additionFractions containing (Z)-2-(6-fluoro-1-indanylidene)acetamide
  5. concentrationconcentrated by spin evaporation in vacuo

出典と根拠

ORDレコード
ord-9f77df6917cf4f368b62e21f32da9bd3
出典データセット
uspto-grants-1999_02
特許番号
US05872118

反応ノート

読み込み中…