반응 #69960

반응 방정식

4-(4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

bromine

→

4-(5-bromo-4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

수율 46.6%

용매

DCM

반응 조건

후처리

1. 1
   온도to warm to ambient and
2. 2
   농축The reaction is concentrated in vacuo
3. 3
   workup.DISSOLUTIONre-dissolved in methanol (10 ml)
4. 4
   workup.ADDITIONpotassium carbonate (250 mg) added
5. 5
   workup.STIRRINGthe resulting suspension stirred at room temperature for a further 17 hours
6. 6
   기타The reaction is quenched by the addition if 2N aqueous HCl (10 ml)
7. 7
   추출extracted with DCM (2×10 ml)
8. 8
   기타The combined organics extracts are dried
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타purified by flash chromatography on silica gel

실험 절차

To a suspension of 4-(4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (73 mg, 0.25 mmol) in DCM (2 ml), at 0° C., is added bromine (26 μl, 0.5 mmol) in one portion, and the reaction allowed to warm to ambient and stirred at room temperature for 3 hours. The reaction is concentrated in vacuo, re-dissolved in methanol (10 ml), potassium carbonate (250 mg) added and the resulting suspension stirred at room temperature for a further 17 hours. The reaction is quenched by the addition if 2N aqueous HCl (10 ml) and extracted with DCM (2×10 ml). The combined organics extracts are dried, filtered, concentrated in vacuo, and purified by flash chromatography on silica gel to give 4-(5-bromo-4-ethyl-2-methyl-thiophen-3-yl)-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione as a brown solid (43 mg).

출처