Methyl phenylacetate → Dimethyl-2-oxo-3-phenylpropyl phosphonate

HRID 28777

Reaktionsgleichung

Reaktionsgleichung von HRID 28777
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].[Li]CCCC.[C:13]1([CH2:19][C:20](OC)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[O:21]=[C:20]([CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Komponenten

5

Edukt 3

HCID 7559Methyl phenylacetateHCID 12958Dimethyl methylphosphonateHCID 178418339Butyllithium

Produkt 1

HCID 12805884Dimethyl-2-oxo-3-phenylpropyl phosphonateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of dimethyl methylphosphonate (2.16 mL, 20 mmol) in anhydrous THF (30 mL), cooled at −78° C. was added n-BuLi (1.6 M in hexane, 13.75 mL, 22 mmol). The mixture was stirred for 30 minutes at this temperature under nitrogen. Methyl phenylacetate (1.40 mL, 10 mmol) was added dropwise for 10 minutes. The mixture was stirred for 2 hours at −78° C., gradually was warm to room temperature. The mixture was quenched with addition of 1N HCl to pH 4-5. The organic layer was separated, washed with brine and dried over MgSO4. The residue was purified through flash chromatography on silica gel (MeOH: CH2Cl2=2:98) to give the product (1.50 g) with colorless oil in 62% yield. 1HNMR (CDCl3, ppm) δ 3.074 (d, J=21 Hz, 2H), 3.760 (s, 3H), 3.762 (s, 3H), 3.86 (s, 2H), 7.31 (m, 5H).

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours at −78° C.
  2. customThe mixture was quenched with addition of 1N HCl to pH 4-5
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified through flash chromatography on silica gel (MeOH: CH2Cl2=2:98)

Quellen und Nachweise

ORD-Eintrag
ord-121122f457ae4f9e8a75c3ceb8d3bddc
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419999B2

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