N,N-Bis(trimethylsilyl)trifluoroacetamide → HCID 178454638, Verbindung

HRID 77348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77348
I[Si](C)(C)C.C([O:8][P:9](OCC)([O:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[CH3:34])=[CH:19]/[C:20]([O:22][C:23]2[C:28]([Cl:29])=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=2[Cl:33])=[O:21])=[CH:14][CH:13]=1)=O)C.C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C>C(Cl)Cl>[PH2:9]([O:11][C:12]1[CH:13]=[CH:14][C:15](/[C:18](/[CH3:34])=[CH:19]/[C:20]([O:22][C:23]2[C:24]([Cl:33])=[C:25]([Cl:32])[C:26]([Cl:31])=[C:27]([Cl:30])[C:28]=2[Cl:29])=[O:21])=[CH:16][CH:17]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 85247Trimethylsilyl iodideHCID 53248609pentachlorophenyl (2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoate

Produkt 1

HCID 178454638HCID 178454638, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe residue was treated with 20 mL of MeCN/H2O (9:1) and 5 drops of conc. HCl for 30 min
  3. concentrationconcentrated in vacuo
  4. additionToluene (5 mL) was added
  5. customevaporated twice
  6. additionOn addition of Et2O solids
  7. customseparated
  8. filtrationwhich were collected by filtration
  9. washwashed with the same solvent
  10. customto give
  11. dry with materialafter drying over P2O5 in vacuo, 1.6 g of 12b as a white powder (88%)
  12. customIt was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-7aea457f0902405aa533806e6b5f45be
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841257B2

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