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

HRID 2216579ノート

反応式

HRID 2216579 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4ab526f3692e48e7bf5315974db91633
出典データセット
uspto-grants-2006_09
特許番号
US07112582B2

反応ノート

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