Formaldehyde → 1alpha-Methyl-6-methylenandrost-4-ene-3,17-dione

HRID 1073702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073702
[CH3:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])=[CH:5][C:4](=[O:22])[CH2:3]1.[CH2:23](OC([O-])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.CNC1C=CC=CC=1.C=O>>[CH3:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6]([C:7](=[CH2:23])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])=[CH:5][C:4](=[O:22])[CH2:3]1

Komponenten

6

Edukt 5

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 7515N-MethylanilineHCID 109575614-Androstene-3,17-dione, 1alpha-methyl-HCID 86744342Diethylorthoformate

Produkt 1

HCID 186420311alpha-Methyl-6-methylenandrost-4-ene-3,17-dioneAusbeute 75 %

Versuchsvorschrift

With a procedure similar to the one described in Example 1, 3 g of 1α-methylandrost-4-ene-3,17-dione, 3 ml of diethylorthoformate, 80 mg of p-toluenesulphonic acid, 1.1 ml of N-methylaniline and 1,2 ml of a 40% formic aldehyde aqueous solution give 2.34 g (75% yield) of the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-cb1ac60841654525870d718055b1d742
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04970327

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