Sodium Iodide → HCID 86734302, compound

HRID 1973742Notes

Reaction equation

HRID 1973742 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH2:7][C:8](=[O:30])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:29])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:4].[I-:31].[Na+]>CC(C)=O>[OH:29][C@@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[C:24](=[O:28])[CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C:8](=[O:30])[CH2:7][CH2:6][O:5][C:3](=[O:4])[CH2:2][I:31])[CH2:17]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86734309HCID 86734309, compound

Product 1

HCID 86734302HCID 86734302, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21-Chloroacetoxymethyl-3α-hydroxy-5α-pregnane-11,20-dione (400 mg.) in acetone (40 ml) was treated with sodium iodide (420 mg.) and the mixture was refluxed for 40 mins. The filtered solution was evaporated to a yellow solid which was partitioned between water and ether/ethyl acetate 1:1. The organic layer was washed with water, dried over sodium sulphate and evaporated to give title compound (500 mg) as a yellow foam.

Workup

  1. temperaturethe mixture was refluxed for 40 mins
  2. customThe filtered solution was evaporated to a yellow solid which
  3. customwas partitioned between water and ether/ethyl acetate 1:1
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-374bd73773794cf7b265a07cf9566e8f
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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