Diethyl methylphosphonate → HCID 86691595, Verbindung

HRID 333945

Reaktionsgleichung

Reaktionsgleichung von HRID 333945
[CH2:1]([O:3][P:4]([CH3:9])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C([Li])CCC.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([N:25]2[CH2:30][CH2:29][N:28]([C:31](OCC)=[O:32])[CH2:27][CH2:26]2)=[CH:17][CH:16]=1.[OH-].[Na+]>C1COCC1.CCCCCC.O.C(O)(=O)C>[CH2:1]([O:3][P:4]([CH2:9][C:31]([N:28]1[CH2:29][CH2:30][N:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]=[CH:16][CH:17]=2)[CH2:26][CH2:27]1)=[O:32])([O:5][CH2:6][CH3:7])=[O:8])[CH3:2]

Komponenten

9

Edukt 4

HCID 12685Diethyl methylphosphonateHCID 14798Sodium HydroxideHCID 66835834HCID 66835834, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 86691595HCID 86691595, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Diethylmethylphosphonate (302.8 mg, 2 mmol) was dissolved in anhydrous THF (2.5 ml), the mixture was cooled to −78° C. under argon, n-butyllithium (2.11 mmol, 846 μl of a 2.5 M solution in hexane) was added dropwise with stirring. After addition was complete, stirring was continued for 20 minutes, after which ethyl 4-(4-quinolyl)piperazine-1-carboxylate (284 mg, 1 mmol) dissolved in 0.5 μl THF was added dropwise. The mixture was allowed to reach room temperature overnight with continued stirring. Glacial acetic acid (0.25 ml) and water (2 ml) was added, after which the mixture was basified with 0.1 NaOH and extracted with diethylether (2×). The organic phases were combined, washed with 5% sodium bicarbonate and water. The aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH and the combined organic phases dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 271 mg (0.693 mmol, 69%). MS (ESI): m/z=392.1 [M+1]+.

Aufarbeitung

  1. additionAfter addition
  2. stirringstirring
  3. additionwas added dropwise
  4. waitto reach room temperature overnight with continued stirring
  5. extractionextracted with diethylether (2×)
  6. washwashed with 5% sodium bicarbonate and water
  7. extractionThe aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH
  8. dry with materialthe combined organic phases dried over magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customto yield 271 mg (0.693 mmol, 69%)

Quellen und Nachweise

ORD-Eintrag
ord-35905a4a66f54338a085c9c0a7ee01a4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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