Pyridine, hydrofluoride (1:1) → HCID 70395782, compound

HRID 1905008Notes

Reaction equation

HRID 1905008 reaction equation
Br[C@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1.C1C=CN=CC=1.[FH:30]>[Hg]=O>[F:30][C@H:2]1[C:19]2[C@:14]([CH3:22])([CH:15]3[CH2:21][C@@H:16]3[C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH2:6]3)[CH2:3]1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 70395582HCID 70395582, compound

Product 1

HCID 70395782HCID 70395782, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 30856Mercuric oxideCatalyst

Procedure

6β-Bromo-1,2β-methylenandrost-4-ene-3,17-dione (0.72 g, 1.9 mmol) is added to a vigorously stirred suspension of yellow mercury (II) oxide (0.83 g, 3.8 mmol) in pyridinium poly (hydrogen fluoride) (7 ml) at room temperature. After 3 hours the mixture is poured onto crushed ice and extracted with dichloromethane. The combined extracts are washed with water, dried and evaporated in vacuo. The residue is chromatographed twice on silica gel using benzene/ethyl ether as eluant to yield pure 6β-fluoro-1,2β-methylenandrost-4-ene-3,17-dione (0.300 g, 50%).

Workup

  1. additionAfter 3 hours the mixture is poured
  2. customonto crushed ice
  3. extractionextracted with dichloromethane
  4. washThe combined extracts are washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue is chromatographed twice on silica gel

Sources & evidence

ORD record
ord-0894fa5ea5344277bae16651a330da74
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

Loading…