Tetrapropylammonium → HCID 21941485, compound

HRID 1158877Notes

Reaction equation

HRID 1158877 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH:16]=[O:17])=[CH:14][C:13]([CH:18]=[O:19])=[N:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>C1COCC1>[O:17]=[C:16]1[C:15]2=[CH:14][C:13]([CH:18]=[O:19])=[N:12][N:11]2[CH2:10][CH2:9][O:8]1

Participants

7

Reactant 5

HCID 9559TetrapropylammoniumHCID 25517Ammonium ChlorideHCID 82029Methyl morpholine oxideHCID 2724141Tetrabutylammonium FluorideHCID 866079681-(2-([tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehyde

Product 1

HCID 21941485HCID 21941485, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehyde (1.02 g, 6.07 mmol) in THF (30 ml) was added 6.68 ml of a 1.0 M solution of tetrabutylammonium fluoride in THF at 0° C. After stirring for 1 hr, the mixture was treated with 10 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The organic solution was washed with brine, dried over anhydrous sodium sulfate, filtered through Magnesol and evaporated. The crude gum was washed with hexanes, dried in vacuo, and then dissolved in methylene chloride (20 ml). To this solution was added 4-methylmorpholine-N-oxide (2.89 g, 24 mmol) and molecular sieve 4 A (6 g). The mixture was stirred at room temperature for 10 min. and then treated with tetrapropylammonium peruthenate (0.11 g, 0.3 mmol). Stirring was continued for 2 hr. The methylene chloride solution was concentrated and diluted with ethyl acetate (40 ml). The mixture was filtered through a pad of silica gel (40 g) and the filter pad was eluted with 2×20 ml ethyl acetate. The combined eluent was washed with 1N HCl and brine, dried over anhydrous sodium sulfate, and evaporated to give 0.30 g of a white solid; mp 135-136° C.; MS m/e 167 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through Magnesol
  5. customevaporated
  6. washThe crude gum was washed with hexanes
  7. customdried in vacuo
  8. dissolutiondissolved in methylene chloride (20 ml)
  9. stirringThe mixture was stirred at room temperature for 10 min.
  10. stirringStirring
  11. waitwas continued for 2 hr
  12. concentrationThe methylene chloride solution was concentrated
  13. additiondiluted with ethyl acetate (40 ml)
  14. filtrationThe mixture was filtered through a pad of silica gel (40 g)
  15. washthe filter pad was eluted with 2×20 ml ethyl acetate
  16. washThe combined eluent was washed with 1N HCl and brine
  17. dry with materialdried over anhydrous sodium sulfate
  18. customevaporated

Sources & evidence

ORD record
ord-02ef31a04efe4959906fdd2482786df9
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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