Dimethylformamide → HCID 68133040, compound

HRID 1578509Notes

Reaction equation

HRID 1578509 reaction equation
[F:1][C:2]1[C:21]2[C@@:16]([CH3:24])([CH:17]3[CH2:23][CH:18]3[C:19](=[O:22])[CH:20]=2)[C@H:15]2[C@H:4]([C@H:5]3[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@:8]([OH:26])([C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]3)[CH:3]=1.[CH3:27]N(C)C=O>CI.[Ag]=O>[F:1][C:2]1[C:21]2[C@@:16]([CH3:24])([CH:17]3[CH2:23][CH:18]3[C:19](=[O:22])[CH:20]=2)[C@H:15]2[C@H:4]([C@H:5]3[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@:8]([O:26][CH3:27])([C:9](=[O:11])[CH3:10])[CH2:7][CH2:6]3)[CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 68132422HCID 68132422, compound

Product 1

HCID 68133040HCID 68133040, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6328Methyl iodideSolvent

Procedure

A solution of 0.35 g of 6-fluoro-17α-hydroxy-1,2-methylene-9β,10α-pregna-4,6-diene-3,20-dione in 35 ml of dimethylformamide and 17.5 ml of methyliodide is stirred at 20°C for 70 hours in the presence of 3.5 g of silver oxide. Then the solid substance is filtered off and the filtrate is extracted subsequent to decanting in water, from methylene chloride and the resultant extract is evaporated to dryness after having been washed to neutral and subsequent to drying. The residue yields, subsequent to chromatography on silicagel, 6-fluoro-17α-methoxy-1,2-methylene-9β,10α-pregna-4,6-diene-3,20-dione.

Workup

  1. filtrationThen the solid substance is filtered off
  2. extractionthe filtrate is extracted subsequent
  3. customto decanting in water, from methylene chloride
  4. extractionthe resultant extract
  5. customis evaporated to dryness
  6. washafter having been washed to neutral and subsequent
  7. customto drying

Sources & evidence

ORD record
ord-43ce36f253a54d7e920b0952e880042a
Source dataset
uspto-grants-1976_02
Patent number
US03937700

Reaction notes

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