Antimony pentafluoride → 5-Nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 49656

反応式

HRID 49656 の反応式
S(F)(=O)(=O)[OH:2].[Sb](F)(F)(F)(F)F.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][C:24]#N)([O-:14])=[O:13]>>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:16]=1[CH2:21][CH2:22][CH2:23][C:24]2=[O:2])([O-:14])=[O:13]

参加物

4

反応物 3

HCID 24557Antimony pentafluorideHCID 24603Fluorosulfuric acidHCID 112177214-(2-Nitrophenyl)butyronitrile

生成物 1

HCID 102619465-Nitro-3,4-dihydronaphthalen-1(2H)-one

反応条件

温度
0 °C

実験手順

1.00 g of fluorosulfuric acid (10 mmol) are added to 1.30 g of antimony(V) fluoride (6 mmol) in a 50 ml glass round-bottomed flask under protective gas and the mixture is cooled to 0° C. Then, 380 mg of 4-(2-nitrophenyl)butyronitrile (2 mmol) are added carefully. The mixture heats up to about 50° C. and is stirred for a farther 12 h at room temperature. The mixture is poured on to ice-cold sodium hydroxide solution, stirring is continued for 30 min at room temperature and then extraction is performed with toluene. Largely complete hydrolysis is made possible by the secondary stirring period. The organic phase is dried over sodium sulfate, filtered off and the solvent is distilled off under reduced pressure. The residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 5:1 v/v). The yield of 5-nitro-3,4-dihydro-1(2H)-naphthalenone is 297 mg with a GC purity of 97% (76% of theoretical value).

後処理

  1. customheats up to about 50° C.
  2. additionThe mixture is poured on to ice-cold sodium hydroxide solution
  3. stirringstirring
  4. waitis continued for 30 min at room temperature
  5. extractionextraction
  6. customLargely complete hydrolysis
  7. stirringsecondary stirring period
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. filtrationfiltered off
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 5:1 v/v)

出典と根拠

ORDレコード
ord-a4715f7798a54648ba8506e8eff2c6d6
出典データセット
uspto-grants-2004_03
特許番号
US06706924B2

関連ノート

読み込み中…