Pyridine → HCID 68126869, compound

HRID 267806Notes

Reaction equation

HRID 267806 reaction equation
N1C=CC=CC=1.[F:7][C@:8]12[C@@H:27]([OH:28])[CH2:26][C@@:25]3([CH3:29])[C@@H:18]([CH2:19][CH:20]=[C:21]3[C:22](=[O:24])[CH3:23])[C@@H:17]1[CH2:16][CH2:15][C:14]1[C@:9]2([CH3:31])[CH2:10][CH2:11][C:12](=[O:30])[CH:13]=1>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[F:7][C@:8]12[C:27](=[O:28])[CH2:26][C@@:25]3([CH3:29])[C@@H:18]([CH2:19][CH:20]=[C:21]3[C:22](=[O:24])[CH3:23])[C@@H:17]1[CH2:16][CH2:15][C:14]1[C@:9]2([CH3:31])[CH2:10][CH2:11][C:12](=[O:30])[CH:13]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 2394059-Fluoro-11-hydroxypregna-4,16-diene-3,20-dione

Product 1

HCID 68126869HCID 68126869, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.5 ml of dry pyridine in 220 ml of dry dichloromethane is added 5.1 g of chromium trioxide in small portions. When all the solid has dissolved, 25 g of dry Celite is added followed (with stirring) by a solution of 3.0 g of 9-fluoro-11β-hydroxypregna-4,16-diene-3,20-dione. The mixture is then stirred at room temperature for 30 minutes, filtered and the solids are washed with a small amount of dichloromethane. The filtrate and the washings are combined, washed with 5% hydrochloric acid, a dilute sodium bicarbonate solution and water, dried and evaporated to afford the product as a solid. One crystallization from acetone-hexane gives 2.65 g of the title compound, melting point 208°-211°C.

Workup

  1. dissolutionWhen all the solid has dissolved
  2. addition25 g of dry Celite is added
  3. filtrationfiltered
  4. washthe solids are washed with a small amount of dichloromethane
  5. washwashed with 5% hydrochloric acid
  6. dry with materiala dilute sodium bicarbonate solution and water, dried
  7. customevaporated

Sources & evidence

ORD record
ord-c78eca59f70c44ebba65167ca0ed1108
Source dataset
uspto-grants-1976_03
Patent number
US03944584

Reaction notes

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