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

HRID 1794518노트

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HRID 1794518 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
200 °C

실험 절차

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]−

후처리

  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)

출처 및 근거

ORD 기록
ord-b9cd899ea475446ebf53eb914bba8a1b
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022733B2

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