Toluene → Methyl 2-acetamidopropanoate

HRID 449187

Reaktionsgleichung

Reaktionsgleichung von HRID 449187
[C:1]([NH:4][C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C(O[K])(C)(C)C.C1(C)C=CC=CC=1>CC(O)(C)C>[C:1]([NH:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 98644Methyl 2-acetamidoacrylateHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 520278Methyl 2-acetamidopropanoateAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Into a 100-mL stainless-steel autoclave was put 143 mg (1 mmol) of methyl 2-acetamido-2-propenate, 22.6 mg [0.03 mmol (Cu reduced)] of [CuBr((S)-SEGPHOS)]n and 33.6 mg (0.3 mmol) of tBuOK, followed by replacing with nitrogen in the autoclave, and then 1.4 mL of a mixed solvent of toluene and t-BuOH in a ratio of 3:1 was added. The reaction was carried out with stirring under a hydrogen pressure of 3.0 MPa at 85° C. for 17 hours to give methyl 2-acetamidopropionate, which is a hydrogenated compound of methyl 2-acetamido-2-propenate in a yield of 52.5%.

Quellen und Nachweise

ORD-Eintrag
ord-3322bd9c3dae45e39713b132bb6beff1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481791B2

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