Butanoic acid, 4-chloro-4-oxo-, ethyl ester → Ethyl 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionate

HRID 452707노트

반응식

HRID 452707 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[NH:14][N:13]=NN=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl[C:16](=[O:24])[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>N1C=CC=CC=1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:24][C:16]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 1784198075-(2,3-dihydro-1-benzofuran-5-yl)-1H-tetrazole

생성물 1

HCID 68664485Ethyl 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionate수율 78.2%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of 5-(2,3-dihydro-1-benzofuran-5-yl)-1H-tetrazole (4.40 g, 23.38 mmol) in pyridine (50 mL) was added ethyl 4-chloro-4-oxobutyrate (4.62 g, 28.06 mmol), and the resulting mixture was stirred at room temperature for 30 min and at 100° C. for 3.5 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, 1M hydrochloric acid, 1M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100) and recrystallized from hexane/ethyl acetate to give the title compound (5.27 g, yield 78%) as pale-yellow crystals.

후처리

  1. temperatureAfter cooling
  2. washwashed with water, 1M hydrochloric acid, 1M aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)
  6. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-da56a99d1e994698986b97684f31b8c9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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