Acetone → HCID 21319892、化合物

HRID 262085ノート

反応式

HRID 262085 の反応式
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.CC(C)=O.C(O)C.[C-:28]#[N:29].[Na+]>O>[C:28]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1)#[N:29]

参加物

6

反応物 4

HCID 180AcetoneHCID 702EthanolHCID 8929Sodium CyanideHCID 13531604HCID 13531604、化合物

生成物 1

HCID 21319892HCID 21319892、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 5-bromomethyl-2-nitro-3-phenylbenzofuran (5 g., 0.015 mole) in 95 ml. of acetone is treated with 20 ml. of ethanol, and the mixture is heated to its reflux temperature. To this mixture is added 0.015 mole of sodium cyanide dissolved in 9 ml. of water, and refluxing is continued for about two hours. The mixture is evaporated under vacuum, then dichloromethane and water are added to the residue. The organic layer is separated, washed with water and dried. The organic layer is then evaporated under vacuum. The residue is purified by eluting twice with benzene through a silica gel column, followed by refluxing in 30 ml. of diethyl ether. The yellow precipitate is separated by filtration and recrystallized twice from benzene to provide 5-cyanomethyl-2-nitro-3-phenylbenzofuran, m.p. 166°-168° C.

後処理

  1. temperaturereflux temperature
  2. dissolutiondissolved in 9 ml
  3. customThe mixture is evaporated under vacuum
  4. additiondichloromethane and water are added to the residue
  5. customThe organic layer is separated
  6. washwashed with water
  7. customdried
  8. customThe organic layer is then evaporated under vacuum
  9. customThe residue is purified
  10. washby eluting twice with benzene through a silica gel column
  11. temperatureby refluxing in 30 ml
  12. customThe yellow precipitate is separated by filtration
  13. customrecrystallized twice from benzene

出典と根拠

ORDレコード
ord-fb4c54cfdf244d80b77c4e87a8dfc74c
出典データセット
uspto-grants-1979_05
特許番号
US04153619

反応ノート

読み込み中…