반응 #1929039

반응 방정식

1-ethylcyclopentyl 2-bromoacetate

5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide

cesium carbonate

→

title compound

수율 94.1%

5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide

수율 94.1%

용매

water

dichloromethane

dimethylformamide

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   추출the aqueous layer extracted with dichloromethane (4×150 mL)
3. 3
   추출The combined organic layers were extracted with water (2×300 mL)
4. 4
   건조dried (Na2SO4)
5. 5
   농축concentrated to the remaining DMF (−100 mL)
6. 6
   workup.ADDITIONThis non-viscous solution was slowly poured onto MTBE (700 mL) under vigorous stirring
7. 7
   여과The precipitate was filtered
8. 8
   세척washed with MTBE (3×200 mL)
9. 9
   기타the residue dried in vacuo

실험 절차

1-ethylcyclopentyl 2-bromoacetate (4.03 g, 17.1 mmol, 1.1 eq) was added dropwise to a solution of 5-(4-hydroxy-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide (6.00 g, 15.6 mmol) and cesium carbonate (10.15 g, 31.1 mmol, 2 eq) in dimethylformamide (150 mL) under N2 at 0° C. The solution was slowly warmed to r.t. and stirred for 16 h. The reaction mixture was diluted with water (400 mL) and dichloromethane (400 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (4×150 mL). The combined organic layers were extracted with water (2×300 mL), dried (Na2SO4) and concentrated to the remaining DMF (−100 mL). This non-viscous solution was slowly poured onto MTBE (700 mL) under vigorous stirring. The precipitate was filtered, washed with MTBE (3×200 mL) and the residue dried in vacuo to afford the title compound (7.92 g, 94%) as a white solid. 1H NMR (500 MHz, d-DMSO) δ: 8.51 (d, J=8 Hz, 2H), 8.32 (d, J=7.5 Hz, 2H), 7.96 (t, J=7.5 Hz, 2H), 7.75 (t, J=7.5 Hz, 2H), 7.31 (s, 2H), 4.51 (s, 2H), 2.21 (s, 6H), 1.93-2.03 (m, 2H), 1.92 (q, J=7 Hz, 2H), 1.49-1.69 (m, 6H), 0.79 (t, J=7 Hz, 3H).

출처