반응 #164530

반응 방정식

Iodotrimethylsilane

11b1

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

bis(trimethylsilyl)trifluoroacetamide

→

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

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   농축The solution was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was treated with 20 mL of MeCN/H2O (9:1) and 5 drops of conc. HCl for 30 min
3. 3
   농축concentrated in vacuo
4. 4
   workup.ADDITIONToluene (5 mL) was added
5. 5
   기타evaporated twice
6. 6
   workup.ADDITIONOn addition of Et2O solids
7. 7
   기타separated
8. 8
   여과which were collected by filtration
9. 9
   세척washed with the same solvent
10. 10
    기타to give
11. 11
    건조after drying over P2O5 in vacuo, 1.6 g of 12b as a white powder (88%)
12. 12
    기타It was used without further purification

실험 절차

Iodotrimethylsilane (2.0 mL, 14.2 mmol) in 5 mL of dry CH2Cl2 was added dropwise to a solution of 11b1 (2.0 g, 3.55 mmol) and bis(trimethylsilyl)trifluoroacetamide (1.8 mL, 7.1 mmol) in 20 mL of dry CH2Cl2 at 0° C. under argon. Stirring was continued for 1 h at 0° C. and 1 h at room temperature. The solution was concentrated in vacuo. The residue was treated with 20 mL of MeCN/H2O (9:1) and 5 drops of conc. HCl for 30 min and concentrated in vacuo. Toluene (5 mL) was added and evaporated twice. On addition of Et2O solids separated, which were collected by filtration and washed with the same solvent to give, after drying over P2O5 in vacuo, 1.6 g of 12b as a white powder (88%). It was used without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 2.6 (s, 3H), 6.6 (s, 1H), 7.24 (d, J=8.7 Hz, 2H), 7.75 (d, J=8.7 Hz, 2H). HRMS (M+H) calc, 503.8658; found, 503.8691.

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