Acetonitrile → (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile

HRID 1022584ノート

反応式

HRID 1022584 の反応式
[C:1](#[N:3])[CH3:2].C([Li])CCC.[Cl:9][C:10]1[CH:11]=[C:12]([C:17](=[O:28])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:13]=[CH:14][C:15]=1[Cl:16]>CCCCCC.C1COCC1.O>[Cl:9][C:10]1[CH:11]=[C:12]([C:17]([OH:28])([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:2][C:1]#[N:3])[CH:13]=[CH:14][C:15]=1[Cl:16]

参加物

7

反応物 3

HCID 6342AcetonitrileHCID 43413487HCID 43413487、化合物HCID 178418339Butyllithium

生成物 1

HCID 66975141(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a mixed solution of acetonitrile (3.54 mL) and THF (30 mL) was added dropwise a solution of n-butyllithium in hexane (1.6 M, 42.1 ml), and the mixture was stirred at −78° C. for 30 min. To the reaction mixture was added dropwise a solution of 1-(3,4-dichlorophenyl)-2-(4-methoxyphenoxy)ethanone (14 g) in THF (45 mL), and the mixture was stirred at −78° C. for 10 min, and then stirred for 1 hr while warming to room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (11.73 g).

後処理

  1. stirringthe mixture was stirred at −78° C. for 10 min
  2. stirringstirred for 1 hr
  3. temperaturewhile warming to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe obtained extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6bb0851c74b34c8f89cec6e7c4f44b9e
出典データセット
uspto-grants-2014_05
特許番号
US08722662B2

反応ノート

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