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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 498894Erstellt: 25. Oktober 2026

3-Benzyloxy-phenylboronic acid → 1,3,5-Trimethoxybenzene

https://huagongshe.com/reaction/498894

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt3-Benzyloxy-phenylboronic acidHCID 2734313—
Eduktmethyl (E)-3-cyclopropyl-2-methyl-3-(4-methylphenyl)sulfonyloxyprop-2-enoateHCID 90357412—
ReagenzPotassium Phosphate, TribasicHCID 62657—
KatalysatorHCID 178479801HCID 178479801—
LösungsmittelWaterHCID 962—
LösungsmittelAcetonitrileHCID 6342—
Produkt1,3,5-TrimethoxybenzeneHCID 69301—
Produkt3-Benzyloxy-phenylboronic acidHCID 2734313—
Produktmethyl (E)-3-cyclopropyl-2-methyl-3-(4-methylphenyl)sulfonyloxyprop-2-enoateHCID 90357412—
Produktmethyl (E)-3-cyclopropyl-2-methyl-3-(3-phenylmethoxyphenyl)prop-2-enoateHCID 90357628—
Produkt(Z)-methyl 3-(3-(benzyloxy)phenyl)-3-cyclopropyl-2-methylacrylateHCID 90357629—
Interner Standard1,3,5-TrimethoxybenzeneHCID 69301—

Reaktionsbedingungen

Temperatur25 °C

Reaktionsschritte

To a 4 ml reaction vial equipped with a magnetic tumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3- (tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg, 0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 µmol) and 1,3,5-trimethoxybenzene (2.17 mg, 0.013 mmol). ACN (1000 µl) and water (10 µl) were added and the mixture agitated to dissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 µl, 0.387 mmol). Finally, to a 96-well sample dilution plate was charged 400 µl of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate buffer.

Herkunft & Nachweise

DOI10.1039/c9re00086k
QuelldatensatzDevelopment of an automated kinetic profiling system with online HPLC for reaction optimization
ORD IDord-c2765f052e4d456ca9fb07cfb28c3328
QuellennotizDevelopment of an automated kinetic profiling system with online HPLC for reaction optimization