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Potassium tert-butoxide → 2-(Methoxymethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

HRID 452819
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HRID 452819 반응식
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1.C[C:29](C)([O-:31])C.[K+]>CO>[CH3:29][O:31][CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1
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참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxide2회HCID 68663800HCID 68663800, 화합물

생성물 1

HCID 686643802-(Methoxymethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole수율 67.4%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

A solution of 2-(chloromethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (0.30 g, 0.76 mmol) and potassium tert-butoxide (85%, 0.12 g, 0.91 mmol) in methanol (5 mL) was stirred overnight at room temperature. Potassium tert-butoxide (85%, 0.03 g, 0.23 mmol) was added to the reaction mixture, and the resulting mixture was stirred at 50° C. overnight. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) and recrystallized from hexane/ethyl acetate to give the title compound (0.20 g, yield 67%) as colorless crystals.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)
  8. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-11c5b0a72dec4d949a765b2a3b71fa86
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492378B2

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