Acetone, oxime → HCID 58928285、化合物

HRID 852090

反応式

HRID 852090 の反応式
CC(=[N:4][OH:5])C.CC(C)([O-])C.[K+].Cl[C:13]1[C:18]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=O)=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:19]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[O:5][N:4]=2)[CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 67180Acetone, oximeHCID 10243711(2-Chloro-pyridin-3-yl)-(3-methoxy-phenyl)-methanoneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 58928285HCID 58928285、化合物収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Combine acetone oxime (3.1 g, 42.4 mmol) in dimethylformamide (15 mL) and add potassium t-butoxide (4.76 g, 42.4 mmol) and stir for 1 hour. Add (2-chloro-pyridin-3-yl)-(3-methoxy-phenyl)-methanone (8.40 g, 34 mmol) dissolved in dimethylformamide (10 mL) and stir at room temperature, overnight. Separate the product between water and ether and evaporate. Purify by column (silica) chromatography (10% ethyl acetate/dichloromethane) and then reflux in a mixture of 1:1 ethanol:5% aqueous hydrochloric acid. Work-up with 5% aqueous sodium hydroxide and ether and purify by flash chromatography (5% ethyl acetate in dichloromethane) to give the title compound (5.21 g, 68% Yield).

後処理

  1. stirringstir at room temperature, overnight
  2. customSeparate the product between water and ether
  3. customevaporate
  4. customPurify by column (silica) chromatography (10% ethyl acetate/dichloromethane)
  5. temperaturereflux in a mixture of 1:1 ethanol
  6. custompurify by flash chromatography (5% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-56ca29a7da0b451cac9253a580723fd2
出典データセット
uspto-grants-2007_08
特許番号
US07253165B2

関連ノート

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