Hydrochloric Acid → Cyano-(4-methoxy-5-methyl-2-nitrophenyl)acetic acid methyl ester

HRID 73338

反応式

HRID 73338 の反応式
[H-].[Na+].[CH3:3][O:4][C:5](=[O:9])[CH2:6][C:7]#[N:8].F[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].Cl>CN(C)C=O>[CH3:3][O:4][C:5](=[O:9])[CH:6]([C:7]#[N:8])[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 598501391-Fluoro-4-methoxy-5-methyl-2-nitrobenzene

生成物 1

HCID 58437260Cyano-(4-methoxy-5-methyl-2-nitrophenyl)acetic acid methyl ester収率 71.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a suspension of sodium hydride (0.86 g) in N,N-dimethylformamide (5 mL) was added dropwise a solution of cyano acetic acid methyl ester (0.35 g) in N,N-dimethylformamide (3 mL) under ice cooling and this mixture was stirred for 15 minutes. To this reaction mixture was added dropwise a solution of 1-fluoro-4-methoxy-5-methyl-2-nitrobenzene (0.44 g) under ice cooling and this mixture was stirred at room temperature for 30 minutes, and then stirred at 70° C. overnight. After cooling to ambient temperature, 1 mol/L hydrochloric acid (5 mL) was added to this reaction mixture. This resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.45 g).

後処理

  1. stirringthis mixture was stirred at room temperature for 30 minutes
  2. stirringstirred at 70° C. overnight
  3. extractionThis resulting mixture was extracted with ethyl acetate
  4. washThis organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-976981bf32554bb7a43ba01cb124ee35
出典データセット
uspto-grants-2014_09
特許番号
US08829040B2

関連ノート

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