Bromotrimethylsilane → [2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl]phosphonic acid

HRID 896987

Reaktionsgleichung

Reaktionsgleichung von HRID 896987
C([O:3][P:4]([CH:9]([NH:17][S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCl>[C:11]1([CH2:10][CH:9]([P:4](=[O:3])([OH:5])[OH:8])[NH:17][S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 76113BromotrimethylsilaneHCID 228909322-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl-phosphonic Acid Diethyl Ester

Produkt 1

HCID 22179290[2-Phenyl-1-(thiophene-2-sulfonylamino)-ethyl]phosphonic acidAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of diethyl phosphonate (xii) (745 mg; 1.8 mmol) in dichloromethane (8 mL) at 0° C. was slowly added bromotrimethylsilane (2 mL; 15.2 mmol). The reaction was gradually warmed to room temperature and the following day the solution was evaporated. The residue was redissolved in dichloromethane (10 mL), evaporated and the process repeated once more. Methanol (10 mL) was added to the residue and the solution stirred at room temperature for 30 minutes, then the solution was filtered and concentrated. The oily residue was triturated with 1:1 ether-hexanes and the orange solid collected by filtration. Finally, the orange solid was boiled in dichloromethane (5 mL), cooled and filtered to yield pure phosphonic acid (xiii) (512 mg, 80%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 2.71 (dt, J=14, 10 Hz, 1H, CHPh), 3.13 (ddd, J=4, 8, 14 Hz, 1H, CHPh), 3.89 (ddd, J=4, 10, 14 Hz, NCHP), 6.86 (dd, J=3.5, 5 Hz, 1H, Ar—H), 7.07-7.15 (m, 6H, Ar—H), 7.53 (dd, J=1.5, 5 Hz, 1H, Ar—H).

Aufarbeitung

  1. customat 0° C.
  2. customthe following day the solution was evaporated
  3. dissolutionThe residue was redissolved in dichloromethane (10 mL)
  4. customevaporated
  5. additionMethanol (10 mL) was added to the residue
  6. filtrationthe solution was filtered
  7. concentrationconcentrated
  8. customThe oily residue was triturated with 1:1 ether-hexanes
  9. filtrationthe orange solid collected by filtration
  10. temperaturecooled
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7ef99151d21b417ebb9d2095ffc9c011
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921756B2

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