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

HRID 2181828
ノート
印刷プレビュー

反応式

HRID 2181828 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

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%);

後処理

  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

出典と根拠

ORDレコード
ord-c4a7df42708845cab072c7f194cb1ad4
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06894061B2

反応ノート

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