Sodium Methoxide → HCID 15840672, 화합물

HRID 342760노트

반응식

HRID 342760 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]([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

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 15840683HCID 15840683, 화합물HCID 53811470HCID 53811470, 화합물

생성물 1

HCID 15840672HCID 15840672, 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 (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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2a074b0605894aec87590c4ad9e8eae8
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859051

반응 노트

불러오는 중…