2-Methoxy-trans-beta-styrylboronic acid pinacol ester synthesis

7synthesis methods

Product Name:2-Methoxy-trans-beta-styrylboronic acid pinacol ester
CAS Number:149777-81-1
Molecular formula:C15H21BO3
Molecular Weight:260.14

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2-Methoxy-trans-beta-styrylboronic acid pinacol ester

149777-81-1
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Yield:149777-81-1 81%

Reaction Conditions:

with C₂₈H₄₀CuNO in acetonitrile at 20; for 2 h;Schlenk technique;Inert atmosphere;

Steps:

A General Protocol

General procedure: To a flame dried Schlenk was added Et₂CAACCuOPh (2.5 mol %) and a magnetic stir bar under an Ar atmosphere. 0.097 mL freshly distilled MeCN was added to fully dissolve catalyst and yield a 2.3 ± 0.1 M solution depending on the nature of the alkyne. Alkyne (0.56 mmol, 1 eq.) was added followed immediately by pinacolborane (0.57 mmol, 1.025 eq). The resulting solution is stirred at room temperature for 2 hours. After this time, the volatiles were evaporated under vacuum. 10 mL pentane was added to residue. This solution was passed through a pad of silica (5 cm diameter x 5 cm high) to remove insoluble components. Elution with 2 x 10 mL of pentane, followed by evaporation under vacuum yielding pure products 2a-m.

References:

Romero, Erik A.;Jazzar, Rodolphe;Bertrand, Guy [Journal of Organometallic Chemistry,2017,vol. 829,p. 11 - 13] Location in patent:supporting information

767-91-9
115 suppliers
$10.00/250mg