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

HRID 2181832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181832
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67553Tetrabutylammonium IodideKatalysator

Versuchsvorschrift

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%);

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b9b96b92b1ae4407a3ab199488e22fe2
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

Notizen zur Reaktion

Wird geladen…