Hydrochloric Acid → HCID 86733129, compound

HRID 1606340Notes

Reaction equation

HRID 1606340 reaction equation
[Na].[CH3:2][O-:3].[Na+].[O:5]1[C@H:7]2[CH2:8][C@H:9]3[C@:24]([CH3:26])([CH2:25][C@@H:6]12)[C@@H:23]1[C@H:12]([C@H:13]2[C@:20]([CH3:28])([CH2:21][C:22]1=[O:27])[C@@H:16]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3.Cl>CO.O>[OH:3][C@@H:2]1[C@@H:6]([O:5][CH3:7])[CH2:25][C@@:24]2([CH3:26])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:27])[CH2:21][C@@:20]2([CH3:28])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 86733130HCID 86733130, compound

Product 1

HCID 86733129HCID 86733129, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium (70 mg.) was dissolved in dry methanol (5 ml.), and to the resulting solution of sodium methoxide (about 166 mg,) was added 2α,3α-epoxy-5α-pregnane-11,20-dione (100 mg). The solution was refluxed for 5 days, then water was added, and the mixture was neutralised with dilute hydrochloric acid and extracted into chloroform. The extract was dried over sodium sulphate and evaporated to a brown oil which was purified by preparative TLC in ethyl acetate/petrol (1/1). The title compound was recrystallised from ethyl acetate/petrol (21 mg).

Workup

  1. temperatureThe solution was refluxed for 5 days
  2. extractionextracted into chloroform
  3. dry with materialThe extract was dried over sodium sulphate
  4. customevaporated to a brown oil which
  5. customwas purified by preparative TLC in ethyl acetate/petrol (1/1)
  6. customThe title compound was recrystallised from ethyl acetate/petrol (21 mg)

Sources & evidence

ORD record
ord-d18885273cfe4f1092f0b0471ad9a609
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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