Tetrapropylammonium → 1-(2-([tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehyde

HRID 2216579Notes

Reaction equation

HRID 2216579 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH2:16][OH:17])=[CH:14][C:13]([CH2:18][OH:19])=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>C(Cl)Cl>[Si:1]([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:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 219414671-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)-1h-pyrazole-3,5dimethanol

Product 1

HCID 866079681-(2-([tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehydeYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dimethanol (1.18 g, 4 mmol) in methylene chloride (20 ml), was added 4-methylmorpholine-N-oxide (2.89 g, 24 mmol) and molecular sieve 4A (4 g). The reaction mixture was stirred at room temperature for 10 min. and then treated with tetrapropylammonium peruthenate (0.15 g, 0.4 mmol). Stirring was continued for 2 hr. The methylene chloride solution was concentrated and diluted with ether (40 ml). The mixture was filtered through a pad of silica gel (40 g) and the filter pad was eluted with 2×20 ml ether. The combined eluent was washed with 1 N HCl and brine, dried over anhydrous sodium sulfate, and evaporated to give 0.79 g of a white solid; mp 63–64° C.; MS m/e 283 (MH+).

Workup

  1. stirringStirring
  2. waitwas continued for 2 hr
  3. concentrationThe methylene chloride solution was concentrated
  4. additiondiluted with ether (40 ml)
  5. filtrationThe mixture was filtered through a pad of silica gel (40 g)
  6. washthe filter pad was eluted with 2×20 ml ether
  7. washThe combined eluent was washed with 1 N HCl and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-4ab526f3692e48e7bf5315974db91633
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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