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

HRID 848782Notes

Reaction equation

HRID 848782 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f1c7cf16dc60433c81cc57197430244e
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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