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Dichloromethane → 5-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol

HRID 2181828
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HRID 2181828 반응식
C[O:2][C:3]1[CH:16]=[C:15]2[C:6]([CH:7]([CH3:29])[N:8]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([CH3:28])[CH:21]=3)(=[O:19])=[O:18])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:8]2[CH:7]([CH3:29])[C:6]3[C:15](=[CH:16][C:3]([OH:2])=[CH:4][CH:5]=3)[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=3)(=[O:19])=[O:18])=[CH:21][C:22]=1[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224822639-Methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

생성물 1

HCID 99998865-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol수율 40%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide
촉매

실험 절차

The title compound was prepared from 9-methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.27 g, 0.66 mmol), tetrabutylammonium iodide (0.61 g, 1.7 mmol), and 1 M boron trichloride in dichloromethane (3.3 mL, 3.3 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient), followed by re-crystallization from a mixture of dichloromethane-hexane, to yield 5-[(4-hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-9-ol as a homogeneous solid (0.10 g, 40%);

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient)
  3. customfollowed by re-crystallization from a mixture of dichloromethane-hexane

출처 및 근거

ORD 기록
ord-c4a7df42708845cab072c7f194cb1ad4
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06894061B2

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