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

HRID 1158876Notes

Reaction equation

HRID 1158876 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 4 A (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 1N 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 1N HCl and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-c9dc162360324417a57161205e71e5ac
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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