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

HRID 1409437노트

반응식

HRID 1409437 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fba620e6f9204df0aeadde4a880b86bd
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921378B2

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