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4-(2-(tert-butyldiMethylsilyloxy)ethyl)-1-trityl-1H-iMidazole synthesis

4synthesis methods
18162-48-6 Synthesis
tert-Butyldimethylsilyl chloride

18162-48-6
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$9.00/5g

127607-62-9 Synthesis
2-(1-trityl-1H-iMidazol-4-yl)ethanol

127607-62-9
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4-(2-(tert-butyldiMethylsilyloxy)ethyl)-1-trityl-1H-iMidazole

928136-82-7
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Yield:928136-82-7 77%

Reaction Conditions:

with 1H-imidazole in dichloromethane at 25;

Steps:

1.3 EXAMPLE 1

[00147j 4-(2-(tert-butvldimethylsilyloxy)ethyl)- 1 -trityl- 1H-imidazole: 2-(1 -Trityl-1H- imidazol-4-yl) ethanol (35 g, 98.75 mmol, 1.00 equiv) was dissolved in DCM (210 mL). To this was added imidazole (19.95 g, 293.05 mmol, 3.00 equiv) and tertbutyldimethylsilylchloride (22.40 g, 149.27 mmol, 1.50 equiv). The mixture was stirred at room temperature until LCMS indicated completion of the reaction. Then the resulting solution was diluted with 500 mL of DCM. The resulting mixture was washed with water (3 x 300 mL). The residue was purified by a silica gel column, eluted with ethyl acetate/petroleum ether (1:4) to afford 40 g (77%) of 4-[2-[(tert- butyldimethylsilyl)oxyj ethyll -1 -(triphenylmethyl)- 1H-imidazole as a white solid. LCMS (ESI): m/z = 469.1 [M+Hf

References:

WO2016/109361,2016,A2 Location in patent:Paragraph 00147