Sodium Iodide → HCID 22789171, compound

HRID 1606350Notes

Reaction equation

HRID 1606350 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:30][C@@:29]2([CH3:31])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:28]2[C:27](=[O:32])[CH2:26][C@@:25]2([CH3:33])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C:22](=[O:24])[CH3:23])[CH2:13][C@@H:12]1[OH:34])=[O:4].[I-:35].[Na+]>CC(C)=O>[OH:34][C@@H:12]1[C@@H:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:3](=[O:4])[CH2:2][I:35])[CH2:30][C@@:29]2([CH3:31])[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:28]2[C:27](=[O:32])[CH2:26][C@@:25]2([CH3:33])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C:22](=[O:24])[CH3:23])[CH2:13]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22789163HCID 22789163, compound

Product 1

HCID 22789171HCID 22789171, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2β-(4'-Chloroacetoxy-n-butoxy)-3α-hydroxy-5α-pregnane-11,20-dione (450 mg.) was dissolved in acetone (30 ml.) and sodium iodide (460 mg.) added to this solution. The mixture was refluxed for 1 hour, a white precipitate forming in this time. The mixture was filtered and the filtrate evaporated to a yellowish solid which was partitioned between ether and water. The ethereal solution was dried over anhydrous sodium sulphate and evaporated in vacuo to give the title compound (467 mg.) as a pale yellow foam which almost immediately collapsed to a gun. This unstable product was used immediately for the following Examples 50 and 51

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customa white precipitate forming in this time
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to a yellowish solid which
  5. customwas partitioned between ether and water
  6. dry with materialThe ethereal solution was dried over anhydrous sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-fda04b70fc5d4506b26f3325e9cb0b3d
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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