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Dimethylformamide → 2-[4-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyloxy]nicotinonitrile

HRID 1294222
ノート
印刷プレビュー

反応式

HRID 1294222 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][OH:24])=[CH:21][CH:20]=1.Cl[C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[CH:30][N:29]=1.CN(C)C=O.[H-].[Na+]>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][O:24][C:28]2[N:29]=[CH:30][CH:31]=[CH:32][C:33]=2[C:34]#[N:35])=[CH:25][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-ChloronicotinonitrileHCID 688833594-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyl alcohol

生成物 1

HCID 688871012-[4-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyloxy]nicotinonitrile収率 78%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

To a mixture of 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyl alcohol (4.00 g), 2-chloro-3-cyanopyridine (2.41 g) and N,N-dimethylformamide (80 mL) was gradually added sodium hydride (60%, oil, 700 mg) under ice-cooling. After stirring the reaction mixture at room temperature for 2 hrs, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. Recrystallization from ethyl acetate-isopropyl ether gave colorless prism crystals (4.02 g, 78%) of 2-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyloxy]nicotinonitrile. melting point: 145-146° C.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-1626ba7f2b6044958bddee4710476e0f
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07238716B2

反応ノート

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