반응 #9769

반응 방정식

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

용매

tetrahydrofuran

—

hexanes

반응 조건

후처리

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

실험 절차

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

출처