Oxalic Acid → HCID 11761638, compound

HRID 1654417Notes

Reaction equation

HRID 1654417 reaction equation
[C:1]([OH:6])(=O)[C:2](O)=[O:3].C1CO[C:14]23OCCO[C:9]2([C@:10]2([CH2:32][C@H:31]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[C@H:30]4[C@@H:21]([CH2:22][CH:23]=[C:24]5[C@@H:29]4[CH2:28][CH2:27][CH2:26][CH2:25]5)[C@@H:12]2[CH2:13]3)[CH3:11])[O:8]1.CO.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:2]1[CH2:1][O:6][C:26]2([CH2:27][CH2:28][C@H:29]3[C:24](=[CH:23][CH2:22][C@@H:21]4[C@@H:30]3[C@@H:31]([C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)[CH2:32][C@@:10]3([CH3:11])[C@H:12]4[CH2:13][CH2:14][C:9]3=[O:8])[CH2:25]2)[O:3]1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 86748619HCID 86748619, compound

Product 1

HCID 11761638HCID 11761638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14 g of silica gel is suspended in 30 ml of methylene chloride, mixed with 1.4 ml of saturated oxalic acid solution and stirred for 15 more minutes. 4.67 g (10 mmol) of 3,3;17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estrene is added to this suspension and the reaction mixture is stirred at room temperature for 4 more hours. Then, it is suctioned off on a frit, the frit residue is rewashed with methanol/methylene chloride and the thus obtained filtrate is shaken out with saturated sodium bicarbonate solution. The organic phase is dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 3.28 g of 3,3-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estren-17-one is obtained as white foam.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 4 more hours
  2. customThe organic phase is dried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-38b8a315eb4746c3bae29533a31f611c
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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