Water → 7beta-Ethyl-estra-1,3,5(10)-trien-17-one

HRID 1005310Notes

Reaction equation

HRID 1005310 reaction equation
[CH2:1]([C@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16][C:17](=O)[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]1)[CH3:2].O.CCOC(C)=O.CCCCCC>C(#N)C>[CH2:1]([C@H:3]1[CH2:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 154550417beta-Ethyl-estr-4-ene-3,17-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 571798617beta-Ethyl-estra-1,3,5(10)-trien-17-oneYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of enone 55 (0.35 g, 1.17 mmol) in acetonitrile (10 mL) was added a CuBr2 (0.31 g, 1.4 mmol) and stirred overnight at room temperature. Water was added until disappearance of the green color, and the acetonitrile was removed under reduced pressure. The residue was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered, and the combined organic layers were washed with water; brine, dried over anhydrous MgSO4, filtered, and concentrated to afford a gum. Chromatography (20% EtOAc/hexane) yielded estrone 56 as a yellow solid (0.28 g, 80%): The major 7α-ethyl isomer of 56: 1H NMR (300 MHz, CDCl3) δ 0.91 (s, 3, CH3), 0.95 (t, J=7.3 Hz, 3, CH2CH3), 6.59 (d, J=2.5 Hz, 1, ArH), 6.65 (dd, J=2.5, 8.4 Hz, 1, ArH), 7.13 (d, J=8.4 Hz, 1, ArH).

Workup

  1. customthe acetonitrile was removed under reduced pressure
  2. extractionThe residue was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. washthe combined organic layers were washed with water
  6. dry with materialbrine, dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a gum

Sources & evidence

ORD record
ord-344823776e314b7dbd7536bca535941e
Source dataset
uspto-grants-2000_04
Patent number
US06054446

Reaction notes

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