Dichloromethane → 5-[(4-Hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol

HRID 2181832ノート

反応式

HRID 2181832 の反応式
C[O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH:5]([CH3:28])[N:6]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=12.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:6]2[CH:5]([CH3:28])[C:4]3[C:3]([OH:2])=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:19])=[O:18])=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823397-Methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

生成物 1

HCID 104066525-[(4-Hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol収率 61%

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

The title compound was prepared from 7-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.17 g, 0.43 mmol), tetrabutylammonium iodide (0.39 g, 1.1 mmol), and 1 M boron trichloride in dichloromethane (2.6 mL, 2.6 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 (1:1), followed by trituration from dichloromethane, to yield 5-[(4-hydroxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol as a homogenous solid (0.096 g, 61%);

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 (1:1)

出典と根拠

ORDレコード
ord-b9b96b92b1ae4407a3ab199488e22fe2
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

反応ノート

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