Tetrahydrofuran → 2,4-Dimethyl-6-phenyl-nicotinonitrile

HRID 1818902

反応式

HRID 1818902 の反応式
[Br-].[Mg+2].[Br-].Cl[C:5]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8].[OH-].[NH4+].[OH-].[Na+].[CH2:24]1COCC1>[Cu](Br)Br>[CH3:24][C:5]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]([CH3:19])[C:6]=1[C:7]#[N:8]

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 82241Magnesium BromideHCID 8336882-Chloro-4-methyl-6-phenylnicotinonitrile

生成物 1

HCID 140902922,4-Dimethyl-6-phenyl-nicotinonitrile収率 55%

試薬・触媒・溶媒 1

HCID 24611Copper bromide (CuBr2)触媒

実験手順

Copper bromide (2.56 g, 17.49 mmol) was suspended in 20 mL of anhydrous THF, dropwisely added with magnesium bromide (3.0M ether, 11.66 mL, 34.99 mmol) at −78° C. and stirred for about 20 minutes. A 10 mL of anhydrous TNF was dropwisely added with a solution, wherein 2 chloro-6-phenyl-4-methyl-nicotinonitrile was dissolved, at the above temperature and then stirred for about 1 hour at room temperature. The mixture was added with a saturated solution of ammonium hydroxide and adjusted its pH to 10 with 1 N NaOH. Then, it was extracted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. A silica gel column chromatography (5% EtOAc/Hexane) was performed on the resulting residue and 550 mg (55%) of 2,4-dimethyl-6-phenyl-nicotinonitrile was obtained in white solid.

後処理

  1. dissolutionwas dissolved, at the above temperature
  2. stirringstirred for about 1 hour at room temperature
  3. extractionThen, it was extracted with ethyl acetate
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5c6b5aac4ccc4e76b5d1180c1520fc4d
出典データセット
uspto-grants-2009_10
特許番号
US07601736B2

関連ノート

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