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

HRID 2216579노트

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HRID 2216579 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-4ab526f3692e48e7bf5315974db91633
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112582B2

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