반응 #69947

반응 방정식

5-Chloro-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanol

sodium hydride

→

5-[2-(4-chloro-phenyl)-thiazol-5-ylmethoxy]-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

수율 96.1%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture is stirred at room temperature overnight
2. 2
   workup.ADDITIONSilica gel is added to the crude
3. 3
   기타reaction mixture
4. 4
   기타the solvent is evaporated under reduced pressure
5. 5
   기타the residue is purified by flash chromatography on silica gel

실험 절차

To a solution of 1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanol (264 mg, 1.1 mmol) in tetrahydrofuran (5 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 44 mg, 1.1 mmol). The reaction mixture is stirred for five minutes at room temperature and 5-Chloro-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (219 mg, 1.1 mmol) is added in one-portion. The reaction mixture is stirred at room temperature overnight. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 5-[2-(4-chloro-phenyl)-thiazol-5-ylmethoxy]-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (410 mg).

출처