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 452707ノート

反応式

HRID 452707 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-da56a99d1e994698986b97684f31b8c9
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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