Triethyl 2-phosphonopropionate → HCID 54386781, Verbindung

HRID 280218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280218
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:37]3[CH:38]=[N:39][CH:40]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=O>O1CCCC1>[CH2:2]([O:3][C:4]([C:6]([CH3:7])=[CH:24][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:37]3[CH:38]=[N:39][CH:40]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:30][CH:31]=1)=[O:5])[CH3:1]

Komponenten

5

Edukt 3

HCID 107155Triethyl 2-phosphonopropionateHCID 2724682Lithium diisopropylamideHCID 136494335-(p-Formylphenyl)-imidazo[1,5-a]pyridine

Produkt 1

HCID 54386781HCID 54386781, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Triethyl 2-phosphonopropionate (0.61 g) is added to a solution of lithium diisopropylamide (from 0.32 g of diisopropylamine and 1.7 ml of 1.64M n-butyllithium) in 20 ml of tetrahydrofuran at 0° under nitrogen. After stirring for 10 minutes, 5-(p-formylphenyl)-imidazo[1,5-a]pyridine (0.50 g) is added dropwise in a solution of 5 ml of tetrahydrofuran. The reaction mixture is stirred for two hours at 0° and quenched with 25 ml of water. The layers are separated and aqueous phase is extracted with ethyl acetate (2×10 ml). The organic phases are combined, dried over sodium sulfate, filtered and evaporated to yield an oil which is chromatographed on silica gel with ethyl acetate as eluent to yield 5-[p-(2-ethoxycarbonylprop-1-enyl)phenyl]imidazo[1,5-a]pyridine; IR (CH2Cl2) 1700 cm-1.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for two hours at 0°
  2. customquenched with 25 ml of water
  3. customThe layers are separated
  4. extractionaqueous phase is extracted with ethyl acetate (2×10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil which
  9. customis chromatographed on silica gel with ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-8d093c0643ed49518a48800d6d67bb1d
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588732

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