1,4-Dioxane → HCID 70638779, compound

HRID 259153Notes

Reaction equation

HRID 259153 reaction equation
[OH:1][C@H:2]1[CH2:25][C@@:24]2([CH3:26])[C@@H:13]([CH2:14][CH2:15][C@:16]2([O:27][C:28](=[O:30])[CH3:29])[C:17](=[O:23])[CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:33])[C:9]([C@@H:10]([F:31])[CH2:11]2)=[CH:8][C:7](=[O:32])[CH2:6][CH2:5]1.O1CCOCC1>C(Cl)(Cl)Cl>[OH:1][C@H:2]1[CH2:25][C@@:24]2([CH3:26])[C@@H:13]([CH2:14][CH2:15][C@:16]2([O:27][C:28](=[O:30])[CH3:29])[C:17](=[O:23])[CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:12]2[C@H:3]1[C@:4]1([CH3:33])[C:9]([C@@H:10]([F:31])[CH2:11]2)=[CH:8][C:7](=[O:32])[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 22798515HCID 22798515, compound

Product 1

HCID 70638779HCID 70638779, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3 g of 11β-hydroxy-17α,21-diacetoxy-6α-fluoro-pregn-4-ene-3,20-dione [compound 4, the product of Example 3] , 2.5 g of 2,3-dichloro-4,5-dicyanobenzoquinone, and 30 ml of dioxan was heated under reflux for 2 hours. The resulting dark colored suspension was cooled, filtered from dichloro-dicyanohydroquinone, and then evaporated to dryness. The residue so obtained was dissolved in chloroform and filtered through neutral alumina (50 g). The solvent was evaporated under reduced pressure. The residue crystallized from methanol as colorless prisms, m.p.: 235°-240°, λmax, 241 nm (ε= 14,200). The analytical sample of 11β-hydroxy-17α,21-diacetoxy-6α-fluoro-pregna-1,4-diene-3,20-dione (compound 5) was obtained by an additional recrystallization from methanol.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe resulting dark colored suspension was cooled
  3. filtrationfiltered from dichloro-dicyanohydroquinone
  4. customevaporated to dryness
  5. customThe residue so obtained
  6. filtrationfiltered through neutral alumina (50 g)
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue crystallized from methanol as colorless prisms, m.p.: 235°-240°, λmax, 241 nm (ε= 14,200)

Sources & evidence

ORD record
ord-774652705e9148dcac3d64ffce66490e
Source dataset
uspto-grants-1977_07
Patent number
US04036831

Reaction notes

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