Sodium Iodide → HCID 86733304, compound

HRID 1606370Notes

Reaction equation

HRID 1606370 reaction equation
Cl[CH2:2][C:3]([O:5][C@@H:6]1[C@@H:25]([O:26][CH2:27][CH3:28])[CH2:24][C@@:23]2([CH3:29])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:30])[CH2:20][C@@:19]2([CH3:31])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16](=[O:18])[CH3:17])[CH2:7]1)=[O:4].[I-:32].[Na+]>CC(C)=O>[CH2:27]([O:26][C@H:25]1[CH2:24][C@@:23]2([CH3:29])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C:21](=[O:30])[CH2:20][C@@:19]2([CH3:31])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16](=[O:18])[CH3:17])[CH2:7][C@@H:6]1[O:5][C:3](=[O:4])[CH2:2][I:32])[CH3:28]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22789166HCID 22789166, compound

Product 1

HCID 86733304HCID 86733304, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3α-Chloroacetoxy-2β-ethoxy-5α-pregnane- 11,20-dione (450 mg) was dissolved in acetone (50 ml) and sodium iodide (460 mg) added to the solution. The mixture was refluxed for one-half hour, a white precipitate forming. The precipitate was filtered off and the filtrate evaporated to a yellow foam which ws partitioned between ether and water. The ethereal solution was dried over anhydrous sodium sulphate and evaporated to give 2β-ethoxy-3α-iodoacetoxy-5α-pregnane-11,20 -dione (460 mg) as a pale yellow foam.

Workup

  1. temperatureThe mixture was refluxed for one-half hour
  2. customa white precipitate forming
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate evaporated to a yellow foam which
  5. customws partitioned between ether and water
  6. dry with materialThe ethereal solution was dried over anhydrous sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-59797fe3e3a441bca5cb57d05ccbf4a0
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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