Sulfuric Acid → HCID 68146911, compound

HRID 1606293Notes

Reaction equation

HRID 1606293 reaction equation
C(O[C@@:5]12[C@@H:22]3[C@@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]1=[CH:9][C:8](=[O:24])[CH:7]=[CH:6]2)(=O)C.[C:25]([O:28]C(=O)C)(=[O:27])[CH3:26].S(=O)(=O)(O)O.[C:37](=[O:40])([O-])[O-].[Na+].[Na+].[CH:43](Cl)(Cl)Cl>>[C:25]([O:28][C:6]1[C:5]2[C@@H:22]3[C@@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C:17](=[O:23])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([O:24][C:37](=[O:40])[CH3:43])[CH:7]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 68146731HCID 68146731, compound

Product 1

HCID 68146911HCID 68146911, compound

Procedure

A suspension of 13.0 g. of 10β-acetoxy-8α-estra-1,4-diene-3,17-dione in 125 ml. of acetic anhydride is mixed dropwise with 0.7 ml. of concentrated sulfuric acid and stirred for 3 hours at room temperature, thus gradually dissolving the substance. The mixture is then introduced into 10 times the amount of ice water to which is added 7 g. of sodium carbonate. The mixture is agitated for 1 hour and then filtered off. The washed and dried residue is recrystallized from methanol, thus obtaining 7 g. of final product, m.p. 208°-211° C. [α]D20 = +89° (CHCl3, c = 0.5).

Workup

  1. additionA suspension of 13.0 g
  2. dissolutionthus gradually dissolving the substance
  3. additionis added 7 g
  4. filtrationfiltered off
  5. washThe washed
  6. customdried residue is recrystallized from methanol
  7. customthus obtaining 7 g

Sources & evidence

ORD record
ord-dda1b4e7243e4d5692526aa45651cbb3
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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