Hydrochloric Acid → HCID 68732160, compound

HRID 1182887Notes

Reaction equation

HRID 1182887 reaction equation
[F:1][C@@H:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](=[O:22])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:21])=[CH:4][C:3]1=[O:23].[Na+].[I-].Cl.C([O-])(O)=O.[Na+]>CC(C)=O.CCOCC>[F:1][C@@H:2]1[CH2:19][C@@:18]2([CH3:20])[CH:5]([C:6](=[O:22])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[OH:21])[CH2:4][C:3]1=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 68733445HCID 68733445, compound

Product 1

HCID 68732160HCID 68732160, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2α-fluoro-17β-hydroxyandrost-4-en-3,6-dione (510 mg) in acetone (76 ml), NaI (950 mg) and conc. HCl (0.51 ml) were added. The mixture was then stirred at RT for 5 min. NaHCO3 was added until neutrality. The organic layer was diluted with Et2O and washed with Na2S2O3 till the brown colour disappeared. The organic phase was washed with H2O and brine, dried over Na2SO4 and was evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/DCM/acetone 5/3/2) to give the title compound in 72% yield.

Workup

  1. washwashed with Na2S2O3 till the brown colour
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. customwas evaporated to dryness
  5. customThe crude reaction mixture
  6. customwas purified by flash chromatography (SiO2, n-hexane/DCM/acetone 5/3/2)

Sources & evidence

ORD record
ord-7ec1edcd7afa40dbbc12df2257ce6fef
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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