Reaction #164529

Reaction equation

10b

(2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoic acid

pentachlorophenol

DCC

→

11b1

Yield 72.2%

pentachlorophenyl (2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoate

Yield 72.2%

Solvents

EtOAc

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered through celite
2. 2
   Otherthe solvent removed in vacuo
3. 3
   OtherThe crude product was purified by silica gel chromatography
4. 4
   Washeluting with 25% EtOac-hexanes

Procedure

A solution of 10b (2.0 g, 6.4 mmol), pentachlorophenol (1.9 g, 7.0 mmol), DCC (1.6 g, 7.7 mmol) and DMAP (0.08 g, 0.64 mmol) in 100 mL of EtOAc was stirred at room temperature for 24 h. The mixture was filtered through celite and the solvent removed in vacuo. The crude product was purified by silica gel chromatography eluting with 25% EtOac-hexanes to give 2.6 g (72%) of 11b1 as white solid. 1H NMR (CDCl3, 300 MHz) δ 1.26-1.32 (m, 6H), 2.54 (d, J=1.2 Hz, 3H), 4.12-4.21 (m, 4H), 6.34 (d, J=1.2 Hz, 1H), 7.2 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H). 11C NMR (CDCl3, 75.0 MHz) δ 16.0, 16.1, 18.4, 64.8, 64.8, 68.9, 113.4, 120.2, 120.3, 128.0, 128.1, 131.2, 131.9, 137.8, 141.9, 144.3, 152.1, 160.6, 161.9. HRMS (M+H) calc, 560.9362; found, 560.9197.

Source