반응 #80993

반응 방정식

ethyl acetate

lithium aluminum hydride

ethyl 2-(N,N-diethylamino)thiazole-4-carboxylate

Rochelle's salt

→

desired compound

수율 73.9%

2-(N,N-Diethylamino)-4-(hydroxymethyl)thiazole

수율 73.9%

용매

toluene

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도to warm slowly to ambient temperature
3. 3
   기타recooled to 0° C.
4. 4
   workup.STIRRINGAfter stirring
5. 5
   여과the slurry was filtered
6. 6
   세척washed with additional ethyl acetate
7. 7
   농축the combined filtrates were concentrated in vacuo
8. 8
   기타The residue was purified by silica gel chromatography

실험 절차

A solution of 3.14 ml of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 30 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 1.43 g (6.28 mmol) of ethyl 2-(N,N-diethylamino)thiazole-4-carboxylate in 5 ml of THF. After addition, the solution was allowed to warm slowly to ambient temperature, stirred for 1 h, recooled to 0° C., and treated with a small amount of aqueous Rochelle's salt followed by ethyl acetate. After stirring, the slurry was filtered, washed with additional ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using methanol in chloroform to provide 0.864 g (73%) of the desired compound, Rf 0.17 (4% methanol in chloroform). Mass spectrum: (M+H)+ =187.

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