Pyridine → 17,17-Ethylenedioxy-2-methoxyestra-1,3,5(10)-trien-3-ol Acetate

HRID 1357474Notes

Reaction equation

HRID 1357474 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]1[CH2:32][O:31][C:10]2([CH2:15][CH2:14][C@H:13]3[C@H:16]4[C@H:25]([CH2:26][CH2:27][C@:11]23[CH3:12])[C:24]2[CH:23]=[C:22]([O:28][CH3:29])C(O)=C[C:19]=2[CH2:18][CH2:17]4)[O:9]1.N1C=CC=CC=1>CO>[C:5]([O:4][C:1]1[C:22]([O:28][CH3:29])=[CH:23][C:24]2[C@@H:25]3[C@H:16]([C@H:13]4[C@@:11]([CH2:27][CH2:26]3)([CH3:12])[C:10]3([O:9][CH2:8][CH2:32][O:31]3)[CH2:15][CH2:14]4)[CH2:17][CH2:18][C:19]=2[CH:2]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 6973620417,17-Ethylenedioxy-2-methoxyestra-1,3,5(10)-trien-3-ol

Product 1

HCID 6973624817,17-Ethylenedioxy-2-methoxyestra-1,3,5(10)-trien-3-ol AcetateYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under nitrogen, acetic anhydride (25 mL, 265 mmol) was added to a solution of the ketal (11) (4.5 g, 13.06 mmol) in dry pyridine (25 mL, 310 mmol). The reaction was stirred overnight at room temperature in the dark. After that time, methanol (50 mL) was added and solvents removed in vacuo. The treatment with methanol was repeated and the residue obtained crystallized from methanol to give the pure 3-acetate (12) (4.85 g, 96%).

Workup

  1. customsolvents removed in vacuo
  2. customthe residue obtained
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-74233f60632c41f6ab5c9abe071e6524
Source dataset
uspto-grants-2003_07
Patent number
US06593321B2

Reaction notes

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