Nitronium tetrafluoroborate → 6-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline

HRID 862564ノート

反応式

HRID 862564 の反応式
[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])[CH:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:6][CH2:5]2.F[B-](F)(F)F.[O:29]=[N+:30]=[O:31]>ClCCl>[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[C:10]([N+:30]([O-:31])=[O:29])[CH:11]=1)[N:8]([C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])[CH:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:6][CH2:5]2

参加物

4

反応物 2

HCID 11073463Nitronium tetrafluoroborateHCID 676514876-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline

生成物 1

HCID 676513916-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline (56.0 g, 0.146 mol) in dichloromethane (500 mL) was added dropwise to a suspension of nitronium tetrafluoroborate (25.0 g, 0.179 mol) in dichloromethane (500 mL) at 0° C. The mixture was stirred for 3 h at 0° C., poured into ice-water and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 3:1 to 2:1 hexane/ethyl acetate to give 52.0 g of the title compound (83%).

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 3:1 to 2:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-6043047cf9c248c8accf7c9ffd9ca1d8
出典データセット
uspto-grants-1998_02
特許番号
US05719152

反応ノート

読み込み中…