Methyl iodide → Methyl 2-(3-chloro-4-cyanophenyl)propanoate

HRID 1428744

反応式

HRID 1428744 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[H-].[Na+].I[CH3:18]>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:18])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3564186Methyl 2-(3-chloro-4-cyanophenyl)acetate

生成物 1

HCID 70855557Methyl 2-(3-chloro-4-cyanophenyl)propanoate収率 65%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of methyl 2-(3-chloro-4-cyanophenyl)acetate (931 mg, 4.441 mmol) in dimethylformamide were added 60% sodium hydride (178 mg, 4.441 mmol) and iodomethane (0.3 mL, 4.441 mmol) at 0° C. The reaction mixture was stirred for 1 h at 0° C., then diluted with water. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give methyl 2-(3-chloro-4-cyanophenyl)propanoate (642 mg, 65%).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-a36f6823ed184d408c51f0b8ce0befca
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

関連ノート

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