Hydrochloric Acid → HCID 70396257, compound

HRID 1905007Notes

Reaction equation

HRID 1905007 reaction equation
[Br:1][C@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1.Cl.O.CCOCC>C(O)(=O)C>[Br:1][C@@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 70395582HCID 70395582, compound

Product 1

HCID 70396257HCID 70396257, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6β-Bromo-1,2β-methylenandrost-4-ene-3,17-dione (200 mg) in acetic acid (15 ml) at 15°-20° is treated with a steady stream of dry hydrogen chloride for 1 hour and then kept an additional hour at room temperature. Then water is added and the product isolated with ether. The combined ether extracts are washed with saturated salt solution, 5% sodium carbonate solution, water; dried and evaporated. Column chromatography of residue over silica gel using benzene/ethyl ether as eluant affords pure 6α-bromo-1,2β-methylenandrost-4-ene-3,17-dione (150 mg, 75%).

Workup

  1. waitkept an additional hour at room temperature
  2. washThe combined ether extracts are washed with saturated salt solution, 5% sodium carbonate solution, water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-ccc7c19c5b664989bf8d02b2899f0133
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

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