Water → HCID 15870673, compound

HRID 1838904Notes

Reaction equation

HRID 1838904 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C:12](=[O:27])[CH2:11][CH2:10]1.[I-:28].[Na+].O>CC(CC)=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]2=[O:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][I:28]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 68949346HCID 68949346, compound

Product 1

HCID 15870673HCID 15870673, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

5.0 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)trien-17-one are dissolved in 80 ml of ethyl methyl ketone, treated with 5.7 g of sodium iodide and stirred overnight at a bath temperature of 90° C. For work-up, the reaction mixture is cooled to room temperature, stirred into water, extracted 3 times with ethyl acetate, washed with sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. 6.8 g of 11β-fluoro-3-hydroxy-7α-(5-iodopentyl)-oestra-1,3,5(10)-trien-17-one are obtained as a crude product, which is employed in the next stage without further purification.

Workup

  1. temperatureFor work-up, the reaction mixture is cooled to room temperature
  2. extractionextracted 3 times with ethyl acetate
  3. washwashed with sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00beeccb3f994aebb96739964c8babd9
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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