Sodium Methoxide → HCID 15840672、化合物

HRID 342760ノート

反応式

HRID 342760 の反応式
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12](=O)N(C)C)=[C:7]([Cl:17])[CH:6]=1.C[O-].[Na+].BrC[CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([CH:31]=[C:32]([CH2:41][CH3:42])[C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1>CO>[Cl:17][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:18])[CH:10]=[CH:9][C:8]=1[S:11][CH2:12][CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([CH:31]=[C:32]([CH2:41][CH3:42])[C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 10942334Sodium MethoxideHCID 15840683HCID 15840683、化合物HCID 53811470HCID 53811470、化合物

生成物 1

HCID 15840672HCID 15840672、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

反応条件

温度
70 °C

実験手順

To a solution of 3-chloro-4-dimethylcarbamoylthiophenylacetic acid methyl ester (54 mg, 0.1656 mmol) in 0.50 mL methanol was added a 0.5M solution of sodium methoxide (0.33 mL, 0.1656 mmol) in methanol. This mixture was heated to 70° C. for 90 minutes. After cooling to ambient temperature, a solution of 7-(3-bromopropoxy)-3-ethyl-8-propylcoumarin (Step D; 54 mg, 0.1656 mmol) in 1.2 mL methanol was added dropwise. The mixture was heated to 70° C. for several hours. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic mixture was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to provide the title compound.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. temperatureThe mixture was heated to 70° C. for several hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic mixture was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2a074b0605894aec87590c4ad9e8eae8
出典データセット
uspto-grants-1999_01
特許番号
US05859051

反応ノート

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