Dichloromethane → 5-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol

HRID 2181830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181830
C[O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH:5]([CH3:29])[N:6]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([CH3:28])[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]([CH3:29])[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][C:22]=1[CH3:28]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823047-Methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Produkt 1

HCID 100453905-[(4-Hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-olAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67553Tetrabutylammonium IodideKatalysator

Versuchsvorschrift

The title compound was prepared from 7-methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.21 g, 0.51 mmol), tetrabutylammonium iodide (0.47 g, 1.3 mmol), and 1 M boron trichloride in dichloromethane (3.1 mL, 3.1 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 3:2 gradient), followed by trituration from dichloromethane, to yield 5-[(4-hydroxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridin-7-ol as a homogeneous solid (0.10 g, 53%), m.p. 258° C.;

Aufarbeitung

  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 3:2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-4332deaba38141ecb11ba1d57d3503b7
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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