Testosterone → HCID 68730646, compound

HRID 1182878Notes

Reaction equation

HRID 1182878 reaction equation
I[CH2:2][CH3:3].[CH3:4][C@@:5]12[C@@H:13]([OH:14])[CH2:12][CH2:11][C@H:10]1[C@@H:9]1[CH2:15][CH2:16][C:17]3[C@@:23]([CH3:24])([C@H:8]1[CH2:7][CH2:6]2)[CH2:22][CH2:21][C:19](=[O:20])[CH:18]=3.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[OH:14][C@H:13]1[CH2:12][CH2:11][C@H:10]2[C@H:9]3[C@H:8]([CH2:7][CH2:6][C@:5]12[CH3:4])[C@:23]1([CH3:24])[C:17](=[C:18]([CH2:2][CH3:3])[C:19](=[O:20])[CH2:21][CH2:22]1)[CH2:16][CH2:15]3

Participants

5

Reactant 3

HCID 6013TestosteroneHCID 6340IodoethaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68730646HCID 68730646, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

Iodoethane (1.60 g) in dry tert-butanol (150 ml) was added dropwise under N2, over 6 h to a vigorously stirred solution heated to reflux, of testosterone (3.00 g) and potassium tert-butoxide (1.75 g) in dry tert-butanol (100 ml). The mixture was refluxed for further 3 h. After cooling to RT, the mixture was quenched by addition of a saturated aqueous NH4Cl solution (170 ml). After stirring for 10 minutes, tert-butanol was evaporated and the mixture was extracted with toluene. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30) to give 17β-hydroxy-4-ethylandrost-4-ene-3-one (1.68 g, 51%).

Workup

  1. temperatureheated
  2. temperatureThe mixture was refluxed for further 3 h
  3. customthe mixture was quenched by addition of a saturated aqueous NH4Cl solution (170 ml)
  4. customtert-butanol was evaporated
  5. extractionthe mixture was extracted with toluene
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30)

Sources & evidence

ORD record
ord-d22155f41f7641c9b809bf49f6def5a7
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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