Sodium Methoxide → HCID 15840670, 화합물

HRID 342756노트

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HRID 342756 반응식
[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]([C:31]([CH2:41][CH3:42])=[CH:32][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]([C:31]([CH2:41][CH3:42])=[CH:32][C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 15840682HCID 15840682, 화합물HCID 15840683HCID 15840683, 화합물

생성물 1

HCID 15840670HCID 15840670, 화합물

시약·촉매·용매 1

HCID 887Methanol용매3회

반응 조건

온도
70 °C

실험 절차

To a solution of 3-chloro-4-dimethylcarbamoylthiophenylacetic acid methyl ester (129 mg, 0.3991 mmol) in 0.75 mL methanol was added a 0.5M solution of sodium methoxide in methanol. This mixture was heated to 70° C. for 90 minutes. After cooling to ambient temperature, a solution of 7-(3-bromopropoxy)-4-ethyl-8-propylcoumarin (Step D) in 1.2 mL methanol was added dropwise. The mixture was heated to 70° C. for 16 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.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. temperatureThe mixture was heated to 70° C. for 16 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)

출처 및 근거

ORD 기록
ord-e0bbc9eb68214549a283e6f6a681b57e
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859051

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