Hydrochloric Acid → Norethandrolone

HRID 1415062Notes

Reaction equation

HRID 1415062 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 2 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-4107e1458a1b4d73b27badf00d3f983a
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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