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

HRID 1828790ノート

反応式

HRID 1828790 の反応式
[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]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 22058664HCID 22058664、化合物HCID 178418244HCID 178418244、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-60 °C

実験手順

4,5-Dibromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole (29.2 g) was dissolved in tetrahydrofuran (250 ml), and 1.63N 1-butyl lithium/hexane solution (58.1 ml) was added dropwise over 20 min at from −55° C. to −60° C. The mixture was stirred at −60° C. for 30 min and N,N-dimethylformamide (58 g) was gradually added dropwise at from −55° C. to −60° C. 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 4-bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-imidazole-5-carbaldehyde (18.5 g) as a pale-yellow oil.

後処理

  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)

出典と根拠

ORDレコード
ord-4d680cf617a14265aa481713b6ba2a56
出典データセット
uspto-grants-2006_06
特許番号
US07060721B1

反応ノート

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