Tetrahydrofuran → HCID 22789160, compound

HRID 1606344Notes

Reaction equation

HRID 1606344 reaction equation
O1[C@H]2C[C@H:5]3[C@:20](C)([CH2:21][C@@H]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.Cl(O)(=O)(=O)=[O:26].[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>O>[OH:30][C@H:34]1[CH2:21][C@@:20]2([CH3:5])[C@@H:31]([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])[CH2:32][C@@H:33]1[OH:26]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24247Perchloric AcidHCID 86733130HCID 86733130, compound

Product 1

HCID 22789160HCID 22789160, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (207 mg.) in hot tetrahydrofuran (6 ml.) was treated with perchloric acid (60%, 0.05 ml.) in tetrahydrofuran (2 ml.) and water (2 ml.). The reaction mixture was concentrated to 5 ml., allowed to stand for 15 minutes and boiled for 30 minutes with the concurrent addition of water. The mixture was poured into ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, dried over sodium sulphate and evaporated to a crystalline mass which was purified by preparative TLC to give the title compound (70 mg.) as colourless crystals, m.p. 194°-198°, [α]D + 103.5°.

Workup

  1. concentrationThe reaction mixture was concentrated to 5 ml
  2. additionboiled for 30 minutes with the concurrent addition of water
  3. additionThe mixture was poured into ethyl acetate
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. extractionThe combined organic extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated to a crystalline mass which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-7a7aaae03b9c4199bea3e64b6a8314ae
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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