2-(2,5-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)ethanone → 2-(4-Hydroxy-phenyl)benzofuran-5-OL

HRID 1794507

반응식

HRID 1794507 반응식
CO[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)=[O:13].Cl.N1C=CC=CC=1>O>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[O:13][C:3]3[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=3[CH:11]=2)=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 3582162-(2,5-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)ethanoneHCID 10176127Pyridinium chloride

생성물 1

HCID 6569362-(4-Hydroxy-phenyl)benzofuran-5-OL수율 51%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
200 °C

실험 절차

A mixture of 74 (1.5 g, 5.2 mmol) and Pyridine HCl (10 g) was heated to 200° C. After 1.5 hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc and the organic layer was dried, concentrated to give a solid which was triturated with CH2Cl2 to give a solid (0.6 g, 51%): Mp=275–278° C.; 1H NMR (DMSO-d6) δ 9.81 (br s, 1 H), 9.12 (br s, 1 H), 7.66 (d, 2 H, J=2.5 Hz), 7.32 (d, 1 H, J=8.5 Hz), 7.00 (s, 1 H), 6.90–6.83 (m, 3 H), 6.65 (dd, 1 H, J=8.6 Hz, 2.6 Hz); MS 225 (M−H)−.

후처리

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with CH2Cl2

출처 및 근거

ORD 기록
ord-8f4f569ca48f43ba8ea62c03fde958a3
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022733B2

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