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

HRID 2364054ノート

反応式

HRID 2364054 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-e63499ebb45142c3bedfa818aad72a34
出典データセット
uspto-grants-2014_04
特許番号
US08691828B2

反応ノート

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