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

HRID 1836021ノート

反応式

HRID 1836021 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, 1H), 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, 2H, 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-6d68f6ef1c9c4ed9a14bd72d312efc72
出典データセット
uspto-grants-2004_08
特許番号
US06774248B2

反応ノート

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