Sodium hydride → 2-Bromo-4,5-dichloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

HRID 1874889ノート

反応式

HRID 1874889 の反応式
[Br:1][C:2]1[NH:3][C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=1.[H-].[Na+].Cl[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[N:3]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 994842-Bromo-4,5-dichloro-1H-imidazoleHCID 516892Sodium BicarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

生成物 1

HCID 586258532-Bromo-4,5-dichloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2-bromo-4,5-dichloro-1H-imidazole (2.16 g, 10 mmol) in THF (25 mL) was added dropwise to a suspension of NaH (440 mg of a 60% suspension in mineral oil, 11 mmol) in THF (20 mL) at 0° C. The mixture was stirred at RT for 2 h, cooled to 0° C. and {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane (1.9 mL, 11 mmol) was added dropwise. The mixture was stirred at RT overnight. Saturated NaHCO3 was added and the aqueous layer was extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (0-50% CH2Cl2/hexanes) to give the title compound (3.26 g, 95%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.26 (2H, s) 3.55-3.61 (2H, m) 0.88-0.94 (2H, m) −0.02 (9H, s). LCMS: m/z 346 (M+1).

後処理

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred at RT overnight
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (0-50% CH2Cl2/hexanes)

出典と根拠

ORDレコード
ord-d5ac7010441044a084068eb38183891d
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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