反应 #1929039

反应方程式

1-ethylcyclopentyl 2-bromoacetate

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

cesium carbonate

→

title compound

收率 94.1%

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

收率 94.1%

溶剂

water

dichloromethane

dimethylformamide

反应条件

后处理

1. 1
   其他The organic layer was separated
2. 2
   萃取the aqueous layer extracted with dichloromethane (4×150 mL)
3. 3
   萃取The combined organic layers were extracted with water (2×300 mL)
4. 4
   干燥dried (Na2SO4)
5. 5
   浓缩concentrated 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
   过滤The precipitate was filtered
8. 8
   洗涤washed with MTBE (3×200 mL)
9. 9
   其他the residue dried in vacuo

实验过程

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).

来源