Azobisisobutyronitrile → Methyl 4-hydroxybenzofuran-2-carboxylate

HRID 2221444ノート

反応式

HRID 2221444 の反応式
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH2:5][CH2:4][CH2:3]1.BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 14494063127724-12-3

生成物 1

HCID 14494065Methyl 4-hydroxybenzofuran-2-carboxylate

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a suspension of methyl 4-oxo-4,5,6,7-tetrahydro-benzofuran-2-ylcarboxylate (5.60 g, 28.8 mmol) in CCl4 (200 ml) were added N-bromosuccinimide (5.18 g, 28.8 mmol) and 2,2′-azobisisobutyronitrile (0.483 g, 2.88 mmol). The reaction mixture was heated at reflux for 80 min and concentrated in vacuo. The residue was suspended in ethyl acetate (200 ml), washed with saturated sodium bicarbonate solution (2×50 ml), brine (50 ml), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel with ethyl acetate/hexane (1/10) to yield methyl 4-hydroxy-benzofuran-2-ylcarboxylate as a while solid (4.21 g, 21.9 mmol).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 80 min
  3. concentrationconcentrated in vacuo
  4. washwashed with saturated sodium bicarbonate solution (2×50 ml), brine (50 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography over silica gel with ethyl acetate/hexane (1/10)

出典と根拠

ORDレコード
ord-be0ff0be9abb4b1b8bafa58ecc59b94c
出典データセット
uspto-grants-2008_05
特許番号
US07368572B2

反応ノート

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