Dimethyl methylphosphonate → [2-(3-Benzyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester

HRID 2184326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184326
[CH3:1][O:2][P:3]([CH3:7])(=[O:6])[O:4][CH3:5].[Li]CCCC.C[O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1>C1COCC1>[CH3:1][O:2][P:3]([CH2:7][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)=[O:14])(=[O:6])[O:4][CH3:5]

Komponenten

5

Edukt 3

HCID 12958Dimethyl methylphosphonateHCID 597640Methyl 3-benzylbenzoateHCID 178418339Butyllithium

Produkt 1

HCID 11359040[2-(3-Benzyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl esterAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a −78° C. THF solution(10 mL) of dimethylmethylphosphonate (0.423 mL, 3.9 mmol) was added 1.6M BuLi in hexanes (2.44 mL, 3.9 mmol). After 1 h a THF solution (5 mL) of 3-benzyl-benzoic acid methyl ester (589 mg, 2.6 mmol) was added. After 15 min. the reaction mixture was warmed to room temperature and stirred an additional 3 h. The reaction mixture was quenched with an aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated. The residue was subjected to column chromatography (18 ethyl acetate: 1 hexanes) to provide [2-(3-benzyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester (677 mg, 2.12 mmol) as an oil.

Aufarbeitung

  1. customTo a −78° C
  2. customThe reaction mixture was quenched with an aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19ecf72669a645b1bfbc2a21d0839934
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900336B2

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