Sodium Iodide → HCID 86733851, compound

HRID 1283725Notes

Reaction equation

HRID 1283725 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C:16](=[O:19])[CH2:17]O)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:26])[CH:4]=[CH:5][C:6](=[O:25])[CH:7]=1.[I-:27].[Na+]>CC(C)=O>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C:16](=[O:19])[CH2:17][I:27])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:26])[CH:4]=[CH:5][C:6](=[O:25])[CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 70580639HCID 70580639, compound

Product 1

HCID 86733851HCID 86733851, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2.0 g of 9-fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione, 21-methanesulfonate in 100 ml of acetone is refluxed with 3 g of sodium iodide under nitrogen for about 17 hours. The solid is filtered off and washed with 50 ml of acetone. The filtrate is evaporated in vacuo. The residue is redissolved in chloroform-methanol (9:1), washed with water, dried over anhydrous sodium sulfate and evaporated in vacuo to give 2.0 g of the title compound.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with 50 ml of acetone
  3. customThe filtrate is evaporated in vacuo
  4. dissolutionThe residue is redissolved in chloroform-methanol (9:1)
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5503ae6e7f024d5aa5f3b86ec4e4f1fc
Source dataset
uspto-grants-1976_08
Patent number
US03976638

Reaction notes

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