Hydrochloric Acid → Norethandrolone

HRID 1077242Notes

Reaction equation

HRID 1077242 reaction equation
[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH2:16][CH:15]=[C:14]([O:21]C)[CH2:13][C:12]=1[CH2:11][CH2:10]3)[CH3:2].Cl>O.CO>[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68143735HCID 68143735, compound

Product 1

HCID 5858NorethandroloneYield 47.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Stir dl-17α-ethyl-3-methoxyestra-2,5(10)-dien-17-ol (1.4 g) with concentrated hydrochloric acid (2.4 ml) in water (1.6 ml) and methanol (36 ml) for two hours. Add water, extract with ether and wash, dry and evaporate the ethereal solution. Recrystallize the product from ethyl acetate-ether to obtain the title compound (0.63 g), m.p. 173°-174.5°; ultraviolet absorption maximum at 240 mμ (ε17,500).

Workup

  1. extractionAdd water, extract with ether
  2. washwash
  3. customdry
  4. customevaporate the ethereal solution
  5. customRecrystallize the product from ethyl acetate-ether

Sources & evidence

ORD record
ord-4f7ca7ba890d44669b3e94f96ce27caa
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…