Water → methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate

HRID 2075430노트

반응식

HRID 2075430 반응식
[I-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O.C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:31]/[C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)=[N:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 178506551HCID 178506551, 화합물

생성물 1

HCID 11952156methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate수율 51.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(1H-indazol-3-ylmethyl)triphenylphosphonium iodide (3.20 g, 6.15 mmol) obtained in Step 4 was dissolved in methanol (60 mL), and the solution was added with methyl p-formylbenzoate (1.00 g, 6.09 mmol) and potassium carbonate (2.55 g, 18.5 mmol), followed by stirring at room temperature overnight. The reaction mixture was added with water, and was extracted with ethyl acetate, then the organic layer was washed with saturated brine, and was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin-layer chromatography (chloroform/methanol=15/1), was further triturated in mixed solvent of ethyl acetate/diisopropyl ether to obtain methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate (0.87 g, 51%).

후처리

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by thin-layer chromatography (chloroform/methanol=15/1)
  6. customwas further triturated in mixed solvent of ethyl acetate/diisopropyl ether

출처 및 근거

ORD 기록
ord-0d14be844ac84a098220e959a7575347
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919517B2

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