반응 #80973

반응 방정식

lithium aluminum hydride

ethyl 2-isopropyl-4-thiazolecarboxylate

Rochelle's salt

→

desired compound

수율 69.3%

4-(Hydroxymethyl)-2-isopropylthiazole

수율 69.3%

용매

ether

toluene

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   workup.STIRRINGAfter stirring
3. 3
   여과the slurry was filtered
4. 4
   세척washed with ethyl acetate
5. 5
   농축the combined filtrates were concentrated in vacuo
6. 6
   기타The residue was purified by silica gel chromatography

실험 절차

A solution of 10 ml (10 mmol) of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 75 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 3.96 g (20 mmol) of ethyl 2-isopropyl-4-thiazolecarboxylate in 10 ml of THF. After addition, the solution was stirred at 0° C. for 3 h, diluted with ether, and treated with a small amount of aqueous Rochelle's salt. After stirring, the slurry was filtered, washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 2.18 g (69%) of the desired compound, Rf 0.58 (4% methanol in chloroform). 1H NMR (CDCl3) δ1.39 (d, J=7 Hz, 6H), 2.94 (br, 1H), 3.31 (heptet, J=7 Hz, 1H), 4.74 (s, 2H), 7.04 (s, 1H). Mass spectrum: (M+H)+ =158.

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