Water → 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-3-carbaldehyde

HRID 1868341ノート

反応式

HRID 1868341 の反応式
[H-].[Na+].Br[C:4]1[C:5]([CH:9]=[O:10])=[N:6][NH:7][CH:8]=1.[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl.O>CN(C=O)C.C(OCC)(=O)C>[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16][N:7]1[CH:8]=[CH:4][C:5]([CH:9]=[O:10])=[N:6]1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178520054HCID 178520054、化合物

生成物 1

HCID 583544901-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-3-carbaldehyde

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride was added slowly to a clear solution of commercially available 4-bromo-1H-pyrazole-3-carbaldehyde Compound 2a (1 g, 3.56 mmol) in DMF (20 mL). The reaction was stirred at ambient temperature for 20 min; then 2-(trimethylsilyl)ethoxy-methyl chloride (755.7 μL, 4.27 mmol) was added dropwise to the reaction mixture. After the resultant solution was stirred at ambient temperature overnight, water (1 mL) was added to quench the reaction. The reaction mixture was diluted with ethyl acetate and washed with water, saturated sodium bicarbonate, and saturated sodium chloride. The organic solvent was dried over magnesium sulfate. After filtration and evaporation of the solvent in vacuo, the crude product was purified by flash chromatography (10:1 to 4:1 hexane/ethyl acetate) to yield (2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-3-carbaldehyde Compound 3a (620 mg, 57% yield) as white solid. 1H NMR (300 MHz, CDCl3) δ 9.97 (s, 1H), 7.64 (s, 1H), 5.81 (s, 2H), 3.62 (t, 2H), 0.93 (t, 2H), 0 (s, 9H); MS (ESI) m/z: 306.7 (M+H+), 328.7 (M+Na+).

後処理

  1. customto quench
  2. customthe reaction
  3. washwashed with water, saturated sodium bicarbonate, and saturated sodium chloride
  4. dry with materialThe organic solvent was dried over magnesium sulfate
  5. filtrationAfter filtration and evaporation of the solvent in vacuo
  6. customthe crude product was purified by flash chromatography (10:1 to 4:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-10fe6efbca744f159aee44ecc35e91be
出典データセット
uspto-grants-2009_12
特許番号
US07635703B2

反応ノート

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