Benzene → H3ST8XN423

HRID 127168Notes

Reaction equation

HRID 127168 reaction equation
C1C=CC=CC=1.[O:7]1[C@@H:31]2[C@:8]31[C@H:17]([C@H:18]1[C@:29]([CH3:32])([CH2:30]2)[C@@:21]([OH:33])([C:22](=[O:28])[CH2:23][O:24][C:25](=[O:27])[CH3:26])[CH2:20][CH2:19]1)[CH2:16][CH2:15][C:14]1[C@:9]3([CH3:35])[CH:10]=[CH:11][C:12](=[O:34])[CH:13]=1.C([CH2:39][C:40]([O-])=[O:41])(C)=C>>[C:40]([O:34][C:12]1[CH:11]=[CH:10][C@@:9]2([CH3:35])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@:8]42[O:7][C@H:31]4[CH2:30][C@@:29]2([CH3:32])[C@H:18]3[CH2:19][CH2:20][C@:21]2([OH:33])[C:22](=[O:28])[CH2:23][O:24][C:25](=[O:27])[CH3:26])[CH:13]=1)(=[O:41])[CH3:39]

Participants

4

Reactant 3

HCID 241BenzeneHCID 118762909beta,11beta-Epoxy-17,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetateHCID 18355900Isopropenylacetate

Product 1

HCID 86737547H3ST8XN423

Procedure

10 g of sulfonic acid resin (Amberlite I R120, marketed by Rohm and Haas Co.) was dehydrated by azeotropic destillation with benzene. The dry resin was suspended in 50 ml isopropenylacetate and 10 g 9β,11β-epoxy-21-acetoxy-17-hydroxy-pregna-1,4-diene-3,20-dione were added. The mixture was heated under reflux for 5 hours, cooled and filtered an the filtrate was evaporated to dryness. The residue which crystallized from methanol (0,5% pyridine) gave in high yield (9,5 grams) 3,21-diacetoxy-17-hydroxy-9β,11β-epoxy-pregna-1,3,5-triene-20-one. Melting point: 194° C., λmax 310 nm (ε5500)⟦alpha⟧sub.D in chloroform -199° C. (c=1% chloroform), νmax (cm-1) (K Br) 3450; 1765; 1740; 1725; 1655; 1625; 1590.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. filtrationfiltered an the filtrate
  5. customwas evaporated to dryness
  6. customThe residue which crystallized from methanol (0,5% pyridine)
  7. customgave

Sources & evidence

ORD record
ord-4fa835e709e2426385a04f0a6c8137c7
Source dataset
uspto-grants-1981_03
Patent number
US04255331

Reaction notes

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