Dimethyl malonate → Dimethyl 2-[2-(2-fluorophenyl)ethyl]malonate

HRID 331239

Reaktionsgleichung

Reaktionsgleichung von HRID 331239
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].CS(O[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])(=O)=O>CN(C=O)C>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][CH:4]([C:3]([O:10][CH3:11])=[O:9])[C:5]([O:7][CH3:8])=[O:6]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 151245352-(2-Fluorophenyl)ethyl methanesulfonate

Produkt 1

HCID 68704652Dimethyl 2-[2-(2-fluorophenyl)ethyl]malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 60% sodium hydride (8.24 g) in DMF (200 ml) was added dropwise dimethyl malonate (24.9 g) under ice-cooling, and the suspension was stirred at 50° C. for 30 min. After cooling to room temperature, a solution of 2-(2-fluorophenyl)ethyl methanesulfonate in DMF (30 ml) was added dropwise, and the mixture was stirred at 150° C. for 1 hr. After cooling to room temperature, the reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give dimethyl 2-[2-(2-fluorophenyl)ethyl]malonate.

Aufarbeitung

  1. temperaturecooling
  2. temperatureAfter cooling to room temperature
  3. stirringthe mixture was stirred at 150° C. for 1 hr
  4. temperatureAfter cooling to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f1eae16853c43fdaf793a333e218356
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877779B2

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