Benzyl Bromide → Benzyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409437ノート

反応式

HRID 1409437 の反応式
[Br:1][C:2]1[N:3]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C.[Ag]=O>[CH2:18]([O:8][C:7]([C:5]1[N:6]=[C:2]([Br:1])[N:3]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1)=[O:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 709813012-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

生成物 1

HCID 70980971Benzyl-2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6342Acetonitrile溶媒

実験手順

Silver oxide (12.7 g, 54.8 mmol) was added to a solution of 2-bromo-1-((2-(trimethyl-silyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (11.7 g, 36.5 mmol) in ACN (200 ml) and stirred at RT for 10 min. Benzyl bromide (4.2 ml, 36.5 mmol) was added to the mixture and stirred at RT for 12 h. The reaction mixture was filtered through a celite bed and the filtrate was concentrated under reduced pressure. The product was purified by flash chromatography. Yield 10 g. 1H-NMR (400 MHz; CDCl3): δ −0.04 (s, 9H), 0.92 (t, 2H), 3.54 (t, 2H), 5.29 (s, 2H), 5.35 (s, 2H), 7.30-7.44 (m, 5H), 7.76 (s, 1H).

後処理

  1. stirringstirred at RT for 12 h
  2. filtrationThe reaction mixture was filtered through a celite bed
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe product was purified by flash chromatography

出典と根拠

ORDレコード
ord-fba620e6f9204df0aeadde4a880b86bd
出典データセット
uspto-grants-2014_12
特許番号
US08921378B2

反応ノート

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