Sodium Iodide → HCID 86736877, compound

HRID 1701453Notes

Reaction equation

HRID 1701453 reaction equation
Cl[CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:31])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:27])[C@@H:10]([O:28][CH2:29][CH3:30])[CH2:9]1)=[O:4].[I-:32].[Na+]>CC(C)=O>[CH2:29]([O:28][C@H:10]1[CH2:9][C@@:8]2([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:7]2[C@@H:6]([O:5][C:3](=[O:4])[CH2:2][I:32])[CH2:25][C@@:24]2([CH3:26])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]1[OH:27])[CH3:30]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86736878HCID 86736878, compound

Product 1

HCID 86736877HCID 86736877, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

11β-Chloroacetoxy-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one (420 mg) in acetone (42 ml) was treated with sodium iodide (550 mg) and the solution was refluxed for one hour, during which time a fine white precipitate formed. The filtered solution was evaporated to an oily solid which was partitioned between ether/ethyl acetate and water. The organic layer was washed with water, dried over sodium sulphate and evaporated to give title compound (510 mg) as a white form, [α]D +80° (c 0.32%).

Workup

  1. temperaturethe solution was refluxed for one hour, during which time a fine white precipitate
  2. customformed
  3. customThe filtered solution was evaporated to an oily solid which
  4. customwas partitioned between ether/ethyl acetate and water
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-e2834183ae7143a88a39670f09734215
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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