Sodium hydride → 4-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole-5-carbaldehyde

HRID 2364054노트

반응식

HRID 2364054 반응식
[Br:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[CH:7]=[O:8].[H-].[Na+].Cl[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=1[CH:7]=[O:8]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27821544-bromo-1H-pyrazole-5-carbaldehyde

생성물 1

HCID 247743744-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole-5-carbaldehyde수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of 4-bromo-1H-pyrazole-5-carbaldehyde (1.93 g, 11 mmol) in THF (50 mL) was added sodium hydride (0.484 g, 12.1 mmol) at 0° C. After 10 min, [2-(chloromethoxy)ethyl](trimethyl)silane (2.34 mL, 13.2 mmol) was added. After 2 h, the mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc (100 mL), and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to 80:20 hexane/EtOAc) to afford the title compound (2.30 g, 69%) as a colorless oil:

후처리

  1. waitAfter 2 h
  2. extractionextracted with EtOAc (100 mL)
  3. dry with materialthe extract was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Purif, silica gel, hexane to 80:20 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e63499ebb45142c3bedfa818aad72a34
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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