Hydrochloric Acid → HCID 54071661, compound

HRID 1606378Notes

Reaction equation

HRID 1606378 reaction equation
C1(C)C=CC(S(O[C@H:11]2[CH2:30][CH2:29][C@@:28]3([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]4[C@@H:27]3[CH2:26][CH2:25][C@@:24]3([CH3:32])[C@H:17]4[CH2:18][CH:19]=[C:20]3[C:21](=[O:23])[CH3:22])[CH2:12]2)(=O)=O)=CC=1.N1C(C)=CC(C)=CC=1C.Cl>>[CH3:22][C:21](=[O:23])[C:20]1[C@:24]2([CH3:32])[C@H:17]([C@H:16]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:31])[C@H:13]([CH2:12][CH:11]=[CH:30][CH2:29]2)[CH2:14][CH2:15]3)[CH2:18][CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 86733309HCID 86733309, compound

Product 1

HCID 54071661HCID 54071661, compoundYield 86.5%

Procedure

3β-Toluene-p-sulphonyloxy-5α-pregn-16-en-20-one (6 g.) was added to hot collidine (12 ml.), and the solution was then refluxed for 30 minutes. The solution was allowed to cool and then poured into cold dilute hydrochloric acid. The precipitate was filtered off, washed with water and dissolved in methylene chloride. The solution was dried over sodium sulphate and then filtered through a short column of silica gel (50 g.). The methylene chloride eluate (about 150 ml.) was evaporated to give 5α-pregna-2,16-dien-20-one (3.29 g.) as white crystals, m.p. 143°-145° , [α]D + 110.5° .

Workup

  1. temperaturethe solution was then refluxed for 30 minutes
  2. temperatureto cool
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. dry with materialThe solution was dried over sodium sulphate
  7. filtrationfiltered through a short column of silica gel (50 g.)
  8. customThe methylene chloride eluate (about 150 ml.) was evaporated

Sources & evidence

ORD record
ord-f59d3f0db3654eb095975deca1a5fcda
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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