Diethyl Ether → 1,16beta-Diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

HRID 839753Notes

Reaction equation

HRID 839753 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].C([O-])(=O)C.C([O-])(=O)C.[Pb+4].C(O[C:22]1[C:39]2[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C:33]([O:40]C(=O)C)=[CH:32][CH2:31]4)[CH2:28][CH2:27][C:26]=2[CH:25]=[C:24]([O:44][CH3:45])[CH:23]=1)(=O)C.CCOCC>C(OC(=O)C)(=O)C.C(O)(=O)C.C1C=CC=CC=1>[C:1]([O:4][C:22]1[C:39]2[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C:33](=[O:40])[C@@H:32]([O:7][C:5](=[O:8])[CH3:6])[CH2:31]4)[CH2:28][CH2:27][C:26]=2[CH:25]=[C:24]([O:44][CH3:45])[CH:23]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 545479651,17-Diacetoxy-3-methoxyestra-1,3,5(10),16-tetraeneHCID 178418268HCID 178418268, compound

Product 1

HCID 540691821,16beta-Diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Lead tetraacetate (0.65 g) is added to a solution of 1,17-diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene (0.5 g, 1.3 mM) in 0.5 ml acetic anhydride and 10 ml glacial acetic acid with stirring. Solution occurs after 1 hr and stirring is continued at room temperature for 16 hrs. The resulting dark brown solution is evaporated in vacuo at 40° to give an oily residue which is dissolved in 150 ml of benzene. The benzene solution is then washed with H2O, 5% NaHCO3 and saturated NaCl solution. The organic layer is dried over MgSO4 and evaporated in vacuo to give a white solid. Trituration with ether gives 1,16β-diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one as a white solid, yield 0.31 g (62%). Recrystallization from methanol gives 1,16β-diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one having a m.p. of 191°-192°.

Workup

  1. stirringstirring
  2. waitis continued at room temperature for 16 hrs
  3. customThe resulting dark brown solution is evaporated in vacuo at 40°
  4. customto give an oily residue which
  5. washThe benzene solution is then washed with H2O, 5% NaHCO3 and saturated NaCl solution
  6. dry with materialThe organic layer is dried over MgSO4
  7. customevaporated in vacuo
  8. customto give a white solid

Sources & evidence

ORD record
ord-2f537cb651d74875981ac68f38594fd6
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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