Water → HCID 67557389, compound

HRID 1415858Notes

Reaction equation

HRID 1415858 reaction equation
C([Al]([CH2:6][CH3:7])CC)C.[C:8]([O:11][CH:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C@H:21]([CH2:22][C:23](=[O:31])[CH:24]=[CH:25]1)[CH2:20][CH2:19]3)(=[O:10])[CH3:9].[Cu](C#N)C#N.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:8]([O:11][CH:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C@H:21]([CH2:22][C:23](=[O:31])[CH2:24][C@@H:25]1[CH2:6][CH3:7])[CH2:20][CH2:19]3)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 16682930TriethylaluminumHCID 67559408HCID 67559408, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 67557389HCID 67557389, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

5.78 ml (11 mmol) of a 1.9 molar solution of triethyl aluminum in toluene is added at room temperature to 3.3 g (10 mmol) of 17-acetoxy-5α-androst-1-en-3-one in 15 ml of ethyl acetate and 44.78 mg (0.5 mmol) of copper cyanide (CuCN). It is stirred 12 hours more at 25° C. The reaction solution is hydrolyzed with 1 ml of water and stirred again for 15 minutes. The inorganic solid is filtered off. The solid is washed again with ethyl acetate. After evaporation of the solvent and chromatography of the substance on silica gel with hexane/ethyl acetate as eluent, 1.44 g (39% of theory) of 17-acetoxy-1α-ethyl-5α-androstan-3-one is obtained.

Workup

  1. stirringstirred again for 15 minutes
  2. filtrationThe inorganic solid is filtered off
  3. washThe solid is washed again with ethyl acetate
  4. customAfter evaporation of the solvent and chromatography of the substance on silica gel with hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-024323fda5ac46ce81a5cd89795560d0
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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