Chlorine → 2alpha-Chloro-17beta-methoxy-5alpha-androstan-3-one

HRID 848782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 848782
[Cl:1]Cl.[CH3:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][C:16](=[O:24])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3>C(O)(=O)C>[Cl:1][C@@H:17]1[CH2:18][C@@:19]2([CH3:20])[C@@H:14]([CH2:13][CH2:12][C@@H:11]3[C@@H:21]2[CH2:22][CH2:23][C@@:6]2([CH3:7])[C@H:8]3[CH2:9][CH2:10][C@@H:5]2[O:4][CH3:3])[CH2:15][C:16]1=[O:24]

Komponenten

4

Edukt 2

HCID 24526ChlorineHCID 1104493517beta-Methoxy-5alpha-androstan-3-one

Produkt 1

HCID 128368592alpha-Chloro-17beta-methoxy-5alpha-androstan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

Chlorine in acetic acid (0.84 M, 12 ml.) is added dropwise with stirring to 17β-methoxy-5α-androstan-3-one (3.0 g.) in acetic acid (10 ml.). When the addition is complete the reaction mixture is chilled, and the precipitate which forms is filtered off, washed with water, dried and recrystallized from acetone-methylene chloride to give the title compound, m.p. 202°-210°; MS (m/e) 338, 306, 302, 291 and 265; NMR (CDCl3) 0.77, 1.10, 3.20, 3.30 and 4.06 δ.

Aufarbeitung

  1. additionWhen the addition
  2. temperatureis chilled
  3. filtrationthe precipitate which forms is filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallized from acetone-methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-f1c7cf16dc60433c81cc57197430244e
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04297350

Notizen zur Reaktion

Wird geladen…