Hydrochloric Acid → (Z)-17beta-hydroxy-2-hydroxymethylene-17alpha-methylandrosta-4,15-dien-3-one

HRID 274313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274313
[CH:1](OCC)=[O:2].[OH:6][C@@:7]1([CH3:27])[CH:12]=[CH:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3.[H-].[Na+].Cl>O1CCCC1.C1(C)C=CC=CC=1>[OH:6][C@@:7]1([CH3:27])[CH:12]=[CH:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:26])/[C:19](=[CH:1]\[OH:2])/[CH2:20]1)[CH2:15][CH2:14]3

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 1567913617beta-Hydroxy-17alpha-methylandrosta-4,15-dien-3-one

Produkt 1

HCID 15679154(Z)-17beta-hydroxy-2-hydroxymethylene-17alpha-methylandrosta-4,15-dien-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At room temperature, 4.6 ml of ethyl formate is added to 4.6 g of 17β-hydroxy-17α-methylandrosta-4,15-dien-3-one in 40 ml of tetrahydrofuran and 70 ml of toluene. Then 3.5 g of sodium hydride (60% paraffin suspension) is added in small portions. After 6 hours, the reaction mixture is gently stirred into ice/water which contains hydrochloric acid, the precipitated product is suctioned off, washed with water, dissolved in methylene chloride, dried, and concentrated under vacuum. After chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient, 2.4 g of (Z)-17β-hydroxy-2-hydroxymethylene-17α-methylandrosta-4,15-dien-3-one is obtained, mp 176° C. (from acetone/hexane).

Aufarbeitung

  1. washwashed with water
  2. dissolutiondissolved in methylene chloride
  3. customdried
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ca2a8c3dd7d4c99b78dc7b6d360a2b1
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389624

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