Sodium Iodide → 4-(3-Oxo-2-propionylpentyl)benzonitrile

HRID 31156

反応式

HRID 31156 の反応式
[H-].[Na+].[CH3:3][CH2:4][C:5](=[O:11])[CH2:6][C:7](=[O:10])[CH2:8][CH3:9].[I-].[Na+].[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)#[N:15]>CC(=O)CC.C(OCC)C>[O:10]=[C:7]([CH2:8][CH3:9])[CH:6]([C:5](=[O:11])[CH2:4][CH3:3])[CH2:20][C:19]1[CH:22]=[CH:23][C:16]([C:14]#[N:15])=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 819233,5-HeptanedioneHCID 869964-(Bromomethyl)benzonitrile

生成物 1

HCID 590181954-(3-Oxo-2-propionylpentyl)benzonitrile収率 58%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

Sodium hydride (60% dispersion in oil, 3.43 g, 86 mmol) was added to a solution of 3,5-heptanedione (10 g, 78 mmol), in 2-butanone (200 ml), under nitrogen. A slight exotherm was observed during gas evolution. Sodium iodide (11.7 g, 78 mmol) was then added, followed by 4-cyanobenzyl bromide (15.29 g, 78 mmol) in 2-butanone (20 ml) and a precipitate was formed. The reaction mixture was heated at reflux for 16 hours. It was then filtered to remove the precipitate and concentrated under reduced pressure. The residue was stirred in dichloromethane (100 ml) and solid sodium bromide was removed by filtration. The dichloromethane filtrate was then washed with water (100 ml) and brine (100 ml). The organic layer was collected, dried over magnesium sulphate and concentrated under reduced pressure to give an orange solid. This was slurried in diethyl ether and filtered off to provide the title compound (11.01 g, 58%) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3): δ=0.98 (t, 6H), 2.29-2.35 (m, 2H), 2.42-2.52 (m, 2H), 3.19 (d, 2H), 3.97 (t, 1H), 7.25 (d, 2H), 7.56 (d, 2H); LRMS: APCl−: m/z 242 [M−H].

後処理

  1. customa precipitate was formed
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 16 hours
  4. filtrationIt was then filtered
  5. customto remove the precipitate
  6. concentrationconcentrated under reduced pressure
  7. customsolid sodium bromide was removed by filtration
  8. washThe dichloromethane filtrate was then washed with water (100 ml) and brine (100 ml)
  9. customThe organic layer was collected
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customto give an orange solid
  13. filtrationfiltered off

出典と根拠

ORDレコード
ord-d7ace11d3202418a94aa69cd11dd3dc1
出典データセット
uspto-grants-2008_09
特許番号
US07425569B2

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