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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 64417Erstellt: 25. Oktober 2026

Toluene → ethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylate

https://huagongshe.com/reaction/64417

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktPotassium Phosphate, TribasicHCID 62657—
Edukt2-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 7018300—
Edukt(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylateHCID 23553751—
Katalysatorpalladium(II) acetateHCID 167845—
LösungsmittelDiethyl EtherHCID 3283—
Produktethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylateHCID 8671342738,6%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A mixture of 1 g of tert-butyl (2-bromobenzyl)carbamate, 1.12 g of ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate, 16 mg of palladium acetate, 72 mg of dicyclohexyl(2′,6′-dimethoxybiophenyl-2-yl)phosphine, 1.5 g of potassium phosphate, and 20 mL of toluene was stirred at 100° C. for 5 days. To the reaction mixture was added ether, followed by filtration through silica gel. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 412 mg of ethyl (2E)-3-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)acrylate.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09447090B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-52bab543b59d45a5b32662ed568d4b3a
Quellennotizuspto-grants-2016_09