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

HRID 1874889노트

반응식

HRID 1874889 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d5ac7010441044a084068eb38183891d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

반응 노트

불러오는 중…