2,6-Lutidine → 3-Methoxy-13beta-methyl-17,17-(ethylenedioxy)gona-1,3,5(10),9(11)-tetraene

HRID 437023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437023
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH3:21])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]14[O:20][CH2:19][CH2:18][O:17]1.CC1C=CC=C(C)N=1>Cl([O-])(=O)(=O)=O.C([N+](CC)(CC)CC)C.CN(C)C=O.CO>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C:9]3=[CH:10][CH2:11][C@@:12]4([CH3:21])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]14[O:17][CH2:18][CH2:19][O:20]1

Komponenten

6

Edukt 2

HCID 79372,6-LutidineHCID 10892807(8'R,9'S,13'S,14'S)-3'-methoxy-13'-methylspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]

Produkt 1

HCID 118095633-Methoxy-13beta-methyl-17,17-(ethylenedioxy)gona-1,3,5(10),9(11)-tetraeneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734932Tetraethylammonium perchlorateKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.3 grams of 3-methoxy-13β-methyl-17,17-(ethylenedioxy)gona-1,3,5(10)-triene, 1.1 milliliters of 2,6-dimethylpyridine, and 1.4 grams of tetraethylammonium perchlorate in 45 milliliters of N,N-dimethylformamide and 50 milliliters of methanol was electrolyzed between the same pair of electrodes that were described in Example 1, spaced from each other at a distance of 1.5 centimeters, with a current of 600 milliamperes for a period of 55 minutes. At the end of the electrolysis all traces of methanol were distilled from the solution at a subatmospheric pressure and the solution was then acidified with anhydrous p-toluenesulfonic acid, allowed to stand at room temperature for a period between 20 and 30 minutes and then made alkaline with a saturated solution of sodium bicarbonate. A portion of the product precipitated during the addition of the bicarbonate solution and water was then added to complete its precipitation. In this manner, 1.8 grams of 3-methoxy-13β-methyl-17,17-(ethylenedioxy)gona-1,3,5-(10),9(11)-tetraene having a melting point of 146°-149° C. was obtained.

Aufarbeitung

  1. distillationAt the end of the electrolysis all traces of methanol were distilled from the solution at a subatmospheric pressure
  2. waitto stand at room temperature for a period between 20 and 30 minutes
  3. customA portion of the product precipitated during the addition of the bicarbonate solution and water
  4. additionwas then added
  5. customits precipitation

Quellen und Nachweise

ORD-Eintrag
ord-7541fec2750f41f1b81f9e0d917af02a
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04029648

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