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

HRID 31156

반응식

HRID 31156 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 590181954-(3-Oxo-2-propionylpentyl)benzonitrile수율 58%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6569Methyl Ethyl Ketone용매2회

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-d7ace11d3202418a94aa69cd11dd3dc1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425569B2

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