反応 #1929042

反応方程式

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

triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

water

→

title compound

収率 93.1%

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

収率 93.1%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他The dichloromethane layer was separated
2. 2
   洗浄the aqueous phase washed with dichloromethane (3×250 mL)
3. 3
   洗浄The combined organic layers were washed with water (4×250 mL)
4. 4
   濃縮concentrated in vacuo and residual water
5. 5
   その他removed via azeotrope with acetonitrile (2×250 mL)

実験手順

5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium bromide (20.0 g, 37.1 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (1.1 eq, 40.8 mmol, 13.5 g) were dissolved in dichloromethane (250 mL) and water (250 mL) and stirred at r.t. overnight. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×250 mL). The combined organic layers were washed with water (4×250 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×250 mL) to afford the title compound (23.8 g, 93%) as a white solid. 1H NMR (300 MHz, (CD3)2CO) δ: 8.53 (d, J=7.8 Hz, 2H), 8.36 (d, J=7.8 Hz, 2H), 8.04 (t, J=7.5 Hz, 2H), 7.83 (t, J=7.8 Hz, 2H), 7.51 (visual s, 2H), 6.14-6.16 (m, 2H), 5.66-5.69 (m, 2H), 4.75 (dd, J=15.6, 15.6 Hz, 2H), 4.57 (s, 2H), 2.30 (s, 6H), 2.03-2.11 (m, 2H), 2.02 (q, J−7.8 Hz, 2H), 1.93-1.95 (m, 3H), 1.55-1.6 (m, 6H), 0.84 (t, J=7.5 Hz, 3H).

出典