Dimethylformamide → 4-Bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole-5-carbaldehyde

HRID 1072801노트

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HRID 1072801 반응식
[Br:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1Br.C([Li])CCC.CCCCCC.CN(C)[CH:30]=[O:31]>O1CCCC1.[Cl-].[Na+].O>[Br:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[CH:30]=[O:31]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 22058664HCID 22058664, 화합물HCID 178418244HCID 178418244, 화합물

생성물 1

HCID 220586064-Bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole-5-carbaldehyde수율 73.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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온도
-60 °C

실험 절차

4,5-Dibromo-2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)imidazol (29.2 g) was dissolved in tetrahydrofurane (250 ml) and a 1.63N n-butyl lithium/hexane solution (58.1 ml) was dropwise added over 20 min at −55° C. to −60° C. The mixture was stirred at −60° C. for 30 min and N,N-dimethylformamide (58 g) was dropwise added at −55° C. to −60° C., and the mixture was stirred at room temperature for 1 hr. Saturated brine was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the objective compound (18.5 g) as a pale-yellow oil.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-572f2c500e024985a4824cbcc8d2f6ec
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911469B2

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