Diethyl Oxalate → Ethyl 7-[(tert-butyldimethylsilyl)oxy]-2,4-dioxoheptanoate

HRID 1595908

Reaktionsgleichung

Reaktionsgleichung von HRID 1595908
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[Na+].[C:15]([Si:19]([CH3:28])([CH3:27])[O:20][CH2:21][CH2:22][CH2:23][C:24](=[O:26])[CH3:25])([CH3:18])([CH3:17])[CH3:16]>>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][O:20][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:27])[CH3:28])[CH3:10]

Komponenten

4

Edukt 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 106802635-[(Tert-butyldimethylsilyl)oxy]pentan-2-one

Produkt 1

HCID 54073086Ethyl 7-[(tert-butyldimethylsilyl)oxy]-2,4-dioxoheptanoateAusbeute 16,6 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diethyl oxalate (4.048 g, 37.7 mmol) was added to solid sodium ethoxide (0.472 g, 69.3 mmol) at 0° C. followed by slow addition of 5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-one (1.500 g, 69.3 mmol). The resulting orange solution was stirred at 0° C. for 10 minutes and at room temperature for 3 h. Purification by flash chromatography (19:1 hexanes:EtOAc to 9:1 EtOAc:MeOH) provided the title compound (1.982 g); MS 317 (M+1).

Aufarbeitung

  1. customPurification by flash chromatography (19:1 hexanes:EtOAc to 9:1 EtOAc:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-27e5f57cbf0242b7b46f3a85fed10a0b
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288120B1

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