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

HRID 2216579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216579
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 866079681-(2-([tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehydeAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4ab526f3692e48e7bf5315974db91633
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112582B2

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