Methyl iodide → 5-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

HRID 2096879ノート

反応式

HRID 2096879 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19](=[O:21])[N:18]([CH3:22])[C:17]=2[CH:23]=1)=[O:12].[H-].[Na+].[CH3:26]I>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:26])[C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19](=[O:21])[N:18]([CH3:22])[C:17]=2[CH:23]=1)=[O:12]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66697114HCID 66697114、化合物

生成物 1

HCID 666971275-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

5-[2-(2-Chloro-5-methoxy-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one (500 mg, obtained in Example 192, step 1) was dissolved in DMF (15 mL). The mixture was cooled to 0° C. To this solution was added sodium hydride (55% in mineral oil, 72 mg). The mixture was stirred for 50 minutes at 0° C. Methyl iodide (0.104 mL) was added dropwise over a period of 10 minutes. Stirring was continued at 0° C. for 1.5 hours. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=7:3) to give the title compound as a colorless gum (312 mg, 60%). MS (m/e)=346.1 [M+H+].

後処理

  1. stirringStirring
  2. waitwas continued at 0° C. for 1.5 hours
  3. extractionextracted two times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=7:3)

出典と根拠

ORDレコード
ord-c2e1b74a348f4245a7faa384781cb4f1
出典データセット
uspto-grants-2013_05
特許番号
US08450313B2

反応ノート

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