Hydrochloric Acid → HCID 18632039, compound

HRID 621630Notes

Reaction equation

HRID 621630 reaction equation
[ClH:1].[F:2][C@@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH3:6])[C:4]1=[O:27])[C@:17]1([CH3:18])[C:12]2(O[CH:13]2[C:14](=[O:23])[CH:15]=[C:16]1[CH3:22])[C:11](=[CH2:25])[C@H:10]3[CH3:26].O>C(O)(=O)C>[F:2][C@@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH3:6])[C:4]1=[O:27])[C@:17]1([CH3:18])[C:12](=[C:13]([Cl:1])[C:14](=[O:23])[CH:15]=[C:16]1[CH3:22])[C:11](=[CH2:25])[C@H:10]3[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 18632037HCID 18632037, compound

Product 1

HCID 18632039HCID 18632039, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Gaseous hydrogen chloride is introduced for about 30 min into a solution of 16α-fluoro-4,5-epoxy-1,7α-dimethyl-6-methylenandrost-1-ene-3,17-dione (359 mg) in glacial acetic acid (5 ml). Thereupon water is added, the precipitate filtered off, washed with diethylether and chromatographed on silica gel to yield pure 16α-fluoro-4-chloro-1,7α-dimethyl-6-methylenandrosta-1,4-diene-3,17-dione (264 mg). Found: C 70.05, H 6.89, Cl 9.32, F 4.99. C22H26ClFO2 requires: C 70.11, H 6.95, Cl 9.41, F 5.04.

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with diethylether
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-7f29a6145fb1406ea469666358a66e4a
Source dataset
uspto-grants-1989_04
Patent number
US04824830

Reaction notes

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