Pyridine → HCID 10339998, Verbindung

HRID 850828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 850828
[CH3:1][O:2][C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C:17]2=[O:21])[C@H:13]2[C@H:4]1[C:5]1[CH:6]=[CH:7][C:8]([OH:22])=[CH:9][C:10]=1[CH2:11][CH2:12]2.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.N1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.O1CCCC1.O1C=CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C@H:3]1[CH2:20][C@@:18]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][C:17]2=[O:21])[C@H:13]2[C@H:4]1[C:5]1[CH:6]=[CH:7][C:8]([O:22][CH:39]3[CH2:38][CH2:37][CH2:36][CH2:35][O:30]3)=[CH:9][C:10]=1[CH2:11][CH2:12]2

Komponenten

8

Edukt 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 1120881311beta-Methoxy-3-hydroxy-estra-1,3,5(10)-trien-17-one

Produkt 1

HCID 10339998HCID 10339998, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 80803,4-dihydro-2H-pyranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 2.0 g of 11β-methoxy-3-hydroxy-estra -1,3,5(10)-trien-17-one in 20 ml of toluene, 5 ml of tetrahydrofuran and 3.0 ml of dihydropyran is stirred with 20 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.5 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 1.9 g of 11β-methoxy-3-tetrahydropyranyloxy-estra -1,3,5(10)-trien-17-one is obtained as crystals with a melting point of 147° C., [α]D22 =+147.2° (c=0.5% in pyridine).

Aufarbeitung

  1. washwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

Quellen und Nachweise

ORD-Eintrag
ord-d42a695279444eb592a0df2f429b74fc
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06018062

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