Ethanol → HCID 12796459, compound

HRID 2049473Notes

Reaction equation

HRID 2049473 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][C:16]1=[O:21])([CH3:14])[C:12](=[O:22])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.C([O-])(O)=O.[Na+].[CH2:28]([OH:30])[CH3:29]>OS(O)(=O)=O>[CH2:28]([O:30][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C:16](=[O:21])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])[CH2:4][C@@H:3]1[OH:1])[CH3:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 12796457HCID 12796457, compound

Product 1

HCID 12796459HCID 12796459, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 2α,3α-epoxy-5α-androstane-11,17-dione (5.0 g) in absolute ethanol (250 ml) was treated with eight drops of fuming H2SO4 at room temperature. After 45 minutes the reaction mixture was treated with aqueous NaHCO3 and evaporated to low volume. Water was added to the mixture which was then refrigerated overnight. The precipitate was collected by filtration, washed with water and dried. Recrystallisation from water-ethanol afforded the title compound (2.1 g), m.p. 164°-167°, [α]D +114°.

Workup

  1. customevaporated to low volume
  2. additionWater was added to the mixture which
  3. customrefrigerated overnight
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. customRecrystallisation from water-ethanol

Sources & evidence

ORD record
ord-2072f424e32d41e99c00c7d1a28d7e89
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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