Sodium Iodide → HCID 54070378, compound

HRID 981353Notes

Reaction equation

HRID 981353 reaction equation
[Br:1][CH:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](Br)([CH2:22]Br)[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:12]2=[O:21])=[CH:4][C:3]1=[O:25].[I-].[Na+]>CC(C)=O>[Br:1][CH:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](=[CH2:22])[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:12]2=[O:21])=[CH:4][C:3]1=[O:25]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 18642033HCID 18642033, compound

Product 1

HCID 54070378HCID 54070378, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 250 ml 3-necked round bottomed flask fitted with a condenser, a thermometer and a magnetic stirrer is charged with 2.68 g of 2,6-dibromo-6-bromomethylandrost-4-ene-3,17-dione, 100 ml of acetone and 5.99 g of sodium iodide. The resulting suspension in refluxed for 15 min, cooled to room temperature, filtered and evaporated in vacuo. The residue is taken up with 50 ml of chloroform, washed twice with a saturated sodium thiosulfate aqueous solution, twice with water and dried over anhydrous calcium chloride. Evaporation of the solvent in vacuo yields 1.86 g of the crude title compound which is directly used for the next step.

Workup

  1. customA 250 ml 3-necked round bottomed flask fitted with a condenser
  2. temperatureThe resulting suspension in refluxed for 15 min
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. washwashed twice with a saturated sodium thiosulfate aqueous solution, twice with water
  6. dry with materialdried over anhydrous calcium chloride
  7. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-e868927ae1f64f7dbecd71f2111ce33f
Source dataset
uspto-grants-1991_02
Patent number
US04990635

Reaction notes

Loading…