HCID 53923971, compound → HCID 54148456, compound

HRID 1196834Notes

Reaction equation

HRID 1196834 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][CH:13]=[CH:14][CH2:15]1)[CH2:10][CH2:9]3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:4][C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C@@H:11]4[C@@H:16]3[CH2:15][CH:14]=[CH:13][CH2:12]4)[C@@H:5]1[CH2:6][CH2:7][C:2]2=[O:1]

Participants

4

Reactant 2

HCID 53923971HCID 53923971, compound2×HCID 131709961Jones' reagent

Product 1

HCID 54148456HCID 54148456, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.18 g of 17β-hydroxy-5α-estr-2-ene, Compound 5, in 10 ml of acetone cooled to 0°-5° C. is added dropwise Jones reagent until the reaction mixture becomes permanently orange-brown. The reaction mixture is stirred for another 2 min, and then the excess reagent is destroyed by addition of isopropanol. The solvent is evaporated under reduced pressure, and the residue is treated with water (25 ml) and ether (25 ml). The ether phase is separated, and the water is extracted once more with ether (20 ml). The combined ether phase is washed with water, sodium chloride solution and dried over sodium sulfate. Evaporation of the solvent produces 0.175 g of 5α-estr-2-ene-17-one.

Workup

  1. customthe excess reagent is destroyed by addition of isopropanol
  2. customThe solvent is evaporated under reduced pressure
  3. additionthe residue is treated with water (25 ml) and ether (25 ml)
  4. customThe ether phase is separated
  5. extractionthe water is extracted once more with ether (20 ml)
  6. washThe combined ether phase is washed with water, sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3949ab9433884d7ea9b0370d39ed78b1
Source dataset
uspto-grants-1992_05
Patent number
US05116830

Reaction notes

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