Perchloric Acid → HCID 22789173, compound

HRID 1606345Notes

Reaction equation

HRID 1606345 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[S-:25][C:26]#[N:27].[K+].P(OP(OP(OP(O)(O)=O)(O)=O)(O)=O)(O)(O)=O.Cl(O)(=O)(=O)=O>O1CCCC1.O>[OH:1][C@@H:3]1[C@@H:2]([S:25][C:26]#[N:27])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4]1

Participants

7

Reactant 4

HCID 24247Perchloric AcidHCID 197147Tetraphosphoric acidHCID 516872Potassium thiocyanateHCID 86733130HCID 86733130, compound

Product 1

HCID 22789173HCID 22789173, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (500 mg.) and potassium thiocyanate (2 g.) in dry tetrahydrofuran (40 ml.) were treated with tetraphosphoric acid (about 2 ml.), and the reaction was stirred at room temperature for 2 hours. Perchloric acid (60%, 0.1 ml.) was added, and after a further 30 minutes the solution was diluted with water and extracted with ether. The extract was washed with water, dried over sodium sulphate and evaporated to give a colourless oil which was purified by preparative tlc and recrystallisation from acetone/petrol to give the title compound, as white prisms m.p. 165°-170° [α]D + 78°.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto give a colourless oil which
  6. customwas purified by preparative tlc and recrystallisation from acetone/petrol

Sources & evidence

ORD record
ord-4fa79c7a6a6a4a3fb15ba9248ec7e84e
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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