Hydrochloric Acid → HCID 86733292, compound

HRID 1606349Notes

Reaction equation

HRID 1606349 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:12]([C:13](=[O:15])[CH3:14])=[CH:11][CH2:10]2)[CH2:7][CH2:6]3.[ClH:25]>C(Cl)(Cl)Cl>[Cl:25][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[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86733293HCID 86733293, compound

Product 1

HCID 86733292HCID 86733292, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2α,3α-Epoxy-5α-pregn-16-ene-11,20-dione (600 mg.) in chloroform (25 ml.) was shaken with concentrated hydrochloric acid (25 ml.) for 2 hours. The organic layer was washed with water, dried over sodium sulphate and evaporated to an oil which was purified by preparative tlc to give 2β-chloro-3α-hydroxy-5α-pregn-16-ene-11,20-dione as the major product. Also isolated was the title compound (75 mg.) as fine white crystals, m.p. 192°-194°, [α]D + 98°.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to an oil which
  4. customwas purified by preparative tlc

Sources & evidence

ORD record
ord-765923f109ea484fac28de25fde22b08
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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