반응 #340387

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lithium aluminum hydride

[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester

[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic Acid Ethyl Ester

→

title compound

수율 72.0%

4-(2-hydroxy-ethyl)-5-methyl-2-(4-trifluoromethyl-phenyl)thiazole

수율 72.0%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONOn complete addition
2. 2
   기타remove the cold bath
3. 3
   workup.ADDITIONDilute the resulting mixture with ethyl acetate
4. 4
   여과filter through a pad of celite
5. 5
   세척Wash the solids with dichloromethane
6. 6
   농축concentrate the combined filtrates under reduced pressure
7. 7
   기타Purify the residue
8. 8
   세척by flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane)

실험 절차

Cool (0° C.) a solution of lithium aluminum hydride (5.3 mL, IM in THF) and add a solution of [5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (Example 1, 1.4 g, 4.25 mmol) in THF (15 mL). On complete addition, remove the cold bath and stir for 2 hrs. Cool this solution to 5° C., and then add water (0.2 mL), dropwise, followed by NaOH solution (0.2 mL, 5M in water) and water (0.2 mL). Dilute the resulting mixture with ethyl acetate and then filter through a pad of celite. Wash the solids with dichloromethane and then concentrate the combined filtrates under reduced pressure. Purify the residue by flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane) to give the title compound as a yellow solid (0.879 g) Use the compound of Example 1 as the starting material to obtain the title compound.

출처