Diethylamine → HCID 53705050, Verbindung

HRID 1845762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845762
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].C1(C)C=CC(S([N:20]=[N+:21]=[N-])(=O)=O)=CC=1.C(NCC)C>CCOCC>[N+:20](=[C:5]([C:4](=[O:10])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH3:9])=[O:7])=[N-:21]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 13661p-Toluenesulfonyl azideHCID 123500Methyl 4-methoxyacetoacetate

Produkt 1

HCID 53705050HCID 53705050, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 4-methoxy-3-oxobutanoate (4.28 g, 0.029 mol) was dissolved in ether (20 mL). The solution was cooled in an ice bath. To the solution was added p-toluenesulfonyl azide (5.78 g, 0.029 mol) followed by N-ethylethanamine (2.0 mL, 0.019 mol). The solution was stirred at 0° C. for 15 minutes, then at rt for 30 minutes. Upon evaporation, the tosyl amide bi-product solidified. This was filtered off and the filtrate was purified by flash chromatography to give the desired product (4.5 g, 89%) as a light oil. 1H NMR (400 MHz, CDCl3): δ 4.55 (s, 2H), 3.83 (s, 3H), 3.45 (s, 3H). MF C6H8N2O4. LCMS calculated for C6H9N2O4(M+H)+: m/z=173.0.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. waitat rt for 30 minutes
  3. customUpon evaporation
  4. filtrationThis was filtered off
  5. customthe filtrate was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15e194b388fb44c4af7fdd9b97194df7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08951536B2

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