Reaktion #164529

Reaktionsgleichung

10b

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

pentachlorophenol

DCC

→

11b1

Ausbeute 72.2%

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

Ausbeute 72.2%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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