Hydrochloric Acid → HCID 86733311, compound

HRID 1606380Notes

Reaction equation

HRID 1606380 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]([CH3:23])([CH2:17][CH2:18]1)[C:12]([C:13](=[O:15])[CH3:14])=[CH:11][CH2:10]2)[CH2:7][CH2:6]3.Cl.O.C(Cl)(Cl)[Cl:27]>C(Cl)Cl>[Cl:27][C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:23])[C@H:9]3[CH2:10][CH:11]=[C:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 86733310HCID 86733310, compound

Product 1

HCID 86733311HCID 86733311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2α,3α-Epoxy-5α-pregn-16-en-20-one (500 mg.) was dissolved in methylene chloride (15 ml.) and concentrated hydrochloric acid (12 ml.) was added. The mixture was shaken for 20 minutes, and then poured into water (100 ml.) and chloroform (100 ml.). The organic layer was separated, washed well with water, dried over sodium sulphate and evaporated to an oil. Recrystallisation from ethyl acetate gave title compound (447 mg.) as colourless crystals, m.p. 246°-252° , [α]D (c, 1.10)+ 65.8° , λmax. (EtOH) 239 nm (ε 8770).

Workup

  1. customThe organic layer was separated
  2. washwashed well with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to an oil
  5. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-380a30b9cc5a415f9fce6771a5d68fc2
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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