Hydrochloric Acid → methyl (2-oxopropoxy)acetate

HRID 478267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478267
C[Zn]C.[C:4]1(C)C=CC=CC=1.Cl[C:12]([CH2:14][O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:13].Cl>[Cl-].[Na+].O.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[O:13]=[C:12]([CH3:4])[CH2:14][O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 12361282Methyl (2-chloro-2-oxoethoxy)acetateHCID 178477796HCID 178477796, Verbindung

Produkt 1

HCID 11701055methyl (2-oxopropoxy)acetateAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)KatalysatorHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2M dimethyl zinc in toluene (21 mL, 42 mmol) was cooled to 0° C. under nitrogen, treated with trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (0.57 g, 76 mmol), treated with methyl 2-(chloroformylmethoxy)acetate (12.6 g, 76 mmol) dropwise over 0.5 hours, stirred for 0.5 hours at 0° C., stirred for 16 hours at ambient temperature, treated with 1M HCl (40 mL) and then brine (20 mL). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography over silica gel (1:2 ethyl acetate/hexanes) to provide the title compound (5.2 g).

Aufarbeitung

  1. stirringstirred for 16 hours at ambient temperature
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography over silica gel (1:2 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ae459b97dd7f46e3aa91d48415cb38c9
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642222B2

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