alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol → (3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone

HRID 54592노트

반응식

HRID 54592 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[OH:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 1

HCID 10565992alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

생성물 1

HCID 10827779(3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone수율 84.9%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매3회HCID 6344Dichloromethane용매

실험 절차

The alcohol (prepared above) (13.4 g, 44.8 mmol) was dissolved in CH2Cl2 (150 ml) and treated with MnO2 (22 g). The reaction mixture was vigorously stirred at RT for 18 h, then treated with a further portion of MnO2 (20 g). More MnO2 (20 g) was added after 10h and the mixture stirred for 18 h, then filtered through Celite® and concentrated in vacuo. The residue was recrystallized from EtOH to afford the title compound (11.27 g; two crops) as a white crystalline solid m.p. 59°-75° C.; δH (CDCl3) 1.5-2.1 (8H,br, m, (CH2)4), 3.88 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.83 (1H, d, J 8.5 Hz, ArH ortho to OMe), and 7.25-7.8 (7H, m, 2×ArH meta to OMe+C6H5); m/z 296 (M+ 11%), 229 (17), 228 (95), 152 (12), 151 (100), 105 (30), 77 (21), and 41 (10).

후처리

  1. stirringthe mixture stirred for 18 h
  2. filtrationfiltered through Celite®
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from EtOH

출처 및 근거

ORD 기록
ord-ce20b3d35aa9447d8950bbbac84e1741
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622977

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