Oxalic Acid → HCID 67597547, compound

HRID 1600989Notes

Reaction equation

HRID 1600989 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([O:16][CH2:17][C:18]23[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]2)[CH2:20][CH2:19]3)(=O)=O)=CC=1.O[C:28]1[CH:45]=[CH:44][C:31]([O:32][CH2:33][CH:34]([OH:43])[CH2:35][CH2:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:30][CH:29]=1.[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48]>CN(C)C=O.[Cl-].[Na+].CCOCC.O>[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48].[C:18]12([CH2:17][O:16][C:28]3[CH:45]=[CH:44][C:31]([O:32][CH2:33][CH:34]([OH:43])[CH2:35][CH2:36][C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[CH:30][CH:29]=3)[CH2:19][CH2:20][CH:21]([CH2:22][CH2:23]1)[CH2:24][CH2:25]2

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 280185bicyclo[2.2.2]oct-1-ylmethyl 4-methylbenzene-1-sulfonateHCID 21830741HCID 21830741, compound

Product 1

HCID 67597547HCID 67597547, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

Anhydrous potassium carbonate (0.100 g) was added to a solution of bicyclo[2,2,2]oct-1-ylmethyl para-toluenesulfonate (0.180 g) and (±)-1-(4-hydroxyphenoxy)-4-(3-pyridyl)-2-butanol (0.115 g) in anhydrous dimethylformamide (3 ml). The mixture was heated at reflux under nitrogen, with stirring for 6 hours then cooled to room temperature before being poured into water (20 ml). The mixture was diluted with saturated aqueous sodium chloride solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with acetone:hexane (2:3) to give an oil. This oil was treated with oxalic acid (excess) in ether to give the title compound as a solid (0.167 g) which was recrystallised from ethyl acetate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with acetone:hexane (2:3)
  8. customto give an oil

Sources & evidence

ORD record
ord-eba4dde1170c4346b319150726329b9c
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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