5-tert-Butyl-2-(4-methoxy-phenyl)-benzofuran → 4-(5-tert-Butyl-benzofuran-2-yl)-phenol

HRID 1794518ノート

反応式

HRID 1794518 の反応式
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:21]=1)([CH3:4])([CH3:3])[CH3:2].Cl.N1C=CC=CC=1>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:10][C:9]=2[CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 101716205-tert-Butyl-2-(4-methoxy-phenyl)-benzofuranHCID 10176127Pyridinium chloride

生成物 1

HCID 101715304-(5-tert-Butyl-benzofuran-2-yl)-phenol収率 17%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
200 °C

実験手順

Compound 84 was treated with Pyridine HCl (5 g) and heated to 200° C. After 1 hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and the crude product was purified by column chromatography (eluant 25% EtOAc/hexanes) to give a solid (0.18 g, 17%); Mp=172–174° C.; 1H NMR (DMSO-d6) δ 9.83 (s, 1 H), 7.70 (d, 2 H, J=8.9 Hz), 7.56 (d, 1 H, J=1.7 Hz), 7.45 (d, 1 H, J=9.0 Hz), 7.32 (dd, 1 H, J=9.0 Hz, 2.1 Hz), 7.11 (s, 1 H), 6.87 (d, 2 H, J=8.5 Hz); MS 265 [M−H]−

後処理

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe crude product was purified by column chromatography (eluant 25% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b9cd899ea475446ebf53eb914bba8a1b
出典データセット
uspto-grants-2006_04
特許番号
US07022733B2

反応ノート

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