Diethyl Carbonate → Diethyl 2-(4-(benzyloxy)phenyl)malonate

HRID 1619433

Reaktionsgleichung

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:23](=O)([O:27]CC)[O:24][CH2:25][CH3:26]>C1COCC1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:23]([O:24][CH2:25][CH3:26])=[O:27])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

To a suspension of NaH (54 gm, 1.11 moles) in dry THF (500 ml) a solution of ethyl 2-(4-(benzyloxy)phenyl)acetate (100 gm, 0.37 moles) in dry THF (100 ml) was added at 0° C. To this was added diethyl carbonate (180 ml, 1.48 mole) dropwise over a period of one hour maintaining the reaction temperature at below 5° C. The reaction mixture was then stirred for 18 hours at 30° C. The contents of the reaction mixture were poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 100 gm of product as white solid.

Aufarbeitung

additionwas added at 0° C
temperaturemaintaining the reaction temperature at below 5° C
additionThe contents of the reaction mixture were poured into ice cold water
extractionextracted with ethyl acetate
extractionThe organic extract
washwas successively washed with water & brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-7d66fd5dc6d64dbd9bd789b81f8ed547
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08772302B2

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