Ethyl Acetate → 2,5-dibromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

HRID 1051705ノート

反応式

HRID 1051705 の反応式
[H-].[Na+].[Br:3][C:4]1[NH:5][C:6]([Br:9])=[CH:7][N:8]=1.[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl.C(OCC)(=O)C>CN(C)C=O>[Br:3][C:4]1[N:5]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:18])([CH3:17])[CH3:10])[C:6]([Br:9])=[CH:7][N:8]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 72048712,4-Dibromo-1H-imidazole

生成物 1

HCID 900427922,5-dibromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole収率 41%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in mineral oil, 0.212 g, 5.30 mmol) was added in portions to a 0° C. solution of 2,5-dibromo-1H-imidazole (0.600 g, 2.67 mmol) in N,N-dimethylformamide (4 mL), and the resulting mixture stirred for 30 min at 0° C. A solution of 2-(trimethylsilyl)ethoxymethyl chloride (0.665 g, 4.01 mmol) in N,N-dimethylformamide (0.5 mL) was added at 0° C., and the resulting solution stirred for an additional 2.5 h at room temperature. The reaction mixture was poured into ethyl acetate (20 mL), washed with brine (3×5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10:1, ethyl acetate/petroleum ether) to afford 2,5-dibromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (0.390 g, 41%) as light yellow oil. MS (ESI, pos. ion) m/z 357, 355, 359 [M+H]+.

後処理

  1. stirringthe resulting solution stirred for an additional 2.5 h at room temperature
  2. washwashed with brine (3×5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified via column chromatography on silica gel (eluting with 10:1, ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-d61f13f0b1c54e32a17adb5f531d3100
出典データセット
uspto-grants-2016_07
特許番号
US09388161B2

反応ノート

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