Ethanol → 2beta-Ethoxy-3alpha-hydroxy-5alpha-androstan-11-one-17beta-carboxylic acid

HRID 267634Notes

Reaction equation

HRID 267634 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@@H:12]([C:22]([OH:24])=[O:23])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)O.O.[CH2:31]([OH:33])[CH3:32]>>[CH2:31]([O:33][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@@H:12]2[C:22]([OH:24])=[O:23])[CH2:4][C@@H:3]1[OH:1])[CH3:32]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 22788254HCID 22788254, compound

Product 1

HCID 227882552beta-Ethoxy-3alpha-hydroxy-5alpha-androstan-11-one-17beta-carboxylic acid

Procedure

A solution of 2α,3α-epoxy-5α-androstan-11-one-17β-carboxylic acid (940 mg.) and concentrated sulphuric acid (0.25 ml.) in dry ethanol (30 ml.) was stirred at room temperature for 30 minutes. Water (100 ml.) was added and the reaction mixture extracted with chloroform. The chloroform solution was washed with water, dried, filtered and evaporated to give a froth which solidified when triturated with chloroform/petrol. Filtration afforded the solid crude product (752 mg.) which, after recrystallisation from ethanol/water, afforded the pure title compound; m.p. 249°-260°; [α]D + 74°, (c 0.33).

Workup

  1. extractionthe reaction mixture extracted with chloroform
  2. washThe chloroform solution was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give a froth which
  7. customtriturated with chloroform/petrol
  8. filtrationFiltration
  9. customafforded the solid crude product (752 mg.) which
  10. customafter recrystallisation from ethanol/water

Sources & evidence

ORD record
ord-3dc92c77d11c46c3acca2060d857e6e2
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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