반응 #43625

반응 방정식

water

tert-butyldimethylsilyl chloride

imidazole

[2-chloro-6-(methyloxy)-4-pyridinyl]methanol

→

desired product

수율 93.0%

2-Chloro-4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)pyridine

수율 93.0%

용매

DMF

반응 조건

후처리

1. 1
   추출extracted three times with dichloromethane
2. 2
   건조dried (magnesium sulphate)
3. 3
   기타evaporated
4. 4
   기타chromatographed on silica gel (100 g)
5. 5
   세척eluting with 1:4 ethyl acetate-hexane

실험 절차

A solution of [2-chloro-6-(methyloxy)-4-pyridinyl]methanol (for a synthesis see Adamczyk, M.; Akireddy, S. R.; Reddy, Rajarathnam E. Tetrahedron 2002, 58(34), 6951)(8.02 g, 46.22 mmol) in dry DMF (100 ml) was treated with tert-butyldimethylsilyl chloride (8.36 g, 55.46 mmol) and imidazole (3.77 g, 55.46 mmol) and stirred at rt for 2 h. The reaction mixture was treated with water extracted three times with dichloromethane, dried (magnesium sulphate), evaporated and chromatographed on silica gel (100 g), eluting with 1:4 ethyl acetate-hexane to give the desired product (12.38 g, 93%).

출처