Hydrochloric Acid → HCID 15513335, compound

HRID 49757Notes

Reaction equation

HRID 49757 reaction equation
[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:19]([CH2:20][CH2:21][C@:3]13[CH3:4])[C@:17]1([CH3:18])[C:12]3(O[CH:13]3[C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]2.[ClH:24].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:24][C:13]1[C:14](=[O:22])[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12]=1[CH2:11][CH2:10][C@@H:9]1[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@@:5]31[CH2:8][C@H:6]3[CH2:7][C@@H:2]2[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 8782849617beta-Hydroxy-4,5-epoxy-14alpha,15alpha-methylene-androstan-3-one

Product 1

HCID 15513335HCID 15513335, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one (1.5 g) is dissolved in 150 mL of acetone and treated at 0° C. with 5.5 mL of concentrated hydrochloric acid. After 24 hours at 0° C., the reaction mixture is neutralized with sodium carbonate solution and the acetone is evaporated. The residue is extracted with dichloromethane. The organic extracts are dried and concentrated. After crystallization from ethanol, 4-chloro-17β-hydroxy-14α,15α-methylene-androst-4-ene-3-one is obtained.

Workup

  1. customthe acetone is evaporated
  2. extractionThe residue is extracted with dichloromethane
  3. customThe organic extracts are dried
  4. concentrationconcentrated
  5. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-456245f79c4a471597f8d42a17d413f7
Source dataset
uspto-grants-2004_03
Patent number
US06710039B1

Reaction notes

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