[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol → 4-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-5-carbaldehyde

HRID 230173노트

반응식

HRID 230173 반응식
[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[CH2:17][OH:18])([O-:3])=[O:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[C:5]=1[CH:17]=[O:18])([O-:3])=[O:2]

참가 물질

4

반응물 1

HCID 68877661[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol

생성물 1

HCID 863462134-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-5-carbaldehyde수율 20.1%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6212Chloroform용매

실험 절차

To a solution of [4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol (7.776 g, 28.38 mmol) in chloroform (500 mL) was added manganese dioxide (29.18 g, 9 eq). The resulting mixture was heated at reflux for 4 hours, cooled to room temperature and stirred overnight. The reaction mixture was again heated to reflux for 3 hours, filtered through a 3 cm plug of celite using additional chloroform. The filtrate was concentrated to give 4.55 g of crude material and purified via silica gel chromatography with a 2-4% ethyl acetate in hexanes gradient to give the title compound as a colorless oil (1.55 g). M+=271

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture was again heated
  4. temperatureto reflux for 3 hours
  5. filtrationfiltered through a 3 cm plug of celite
  6. concentrationThe filtrate was concentrated
  7. customto give 4.55 g of crude material
  8. custompurified via silica gel chromatography with a 2-4% ethyl acetate in hexanes gradient

출처 및 근거

ORD 기록
ord-0c46d585439c4aa1a453792492cf4446
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566708B2

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