Reacción #9769

Ecuación de reacción

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

triisopropyl[(3-methylthien-2-yl)methoxy]silane

intermediate 115

triisopropyl[(3-methylthien-2-yl)methoxy]silane

butyllithium

ammonium chloride

→

title compound

triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane

Disolventes

tetrahydrofuran

—

hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturare-cooled to −78° C
2. 2
   workup.STIRRINGthe reaction stirred at this temperature for 4 hours
3. 3
   Temperaturawarmed to 0° C
4. 4
   ExtracciónThe aqueous mixture was extracted with diethyl ether
5. 5
   Secadothe organic solution dried with brine and over sodium sulfate
6. 6
   OtroEvaporation of the solvent

Procedimiento

A mixture of triisopropyl[(3-methylthien-2-yl)methoxy]silane (intermediate 115, 1.42 g) in tetrahydrofuran (20 ml), stirred at −78° C. under nitrogen, was treated with 1.6M butyllithium in hexanes (3.9 ml). The reaction temperature was slowly allowed to rise to 0° C. over 2 hours and then re-cooled to −78° C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.28 ml) was added and the reaction stirred at this temperature for 4 hours and then warmed to 0° C. The reaction was added to a mixture of saturated ammonium chloride and ice. The aqueous mixture was extracted with diethyl ether and the organic solution dried with brine and over sodium sulfate. Evaporation of the solvent afforded the title compound as a white solid

Fuente