反応 #9769

反応方程式

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

溶媒

tetrahydrofuran

—

hexanes

反応条件

後処理

1. 1
   温度re-cooled to −78° C
2. 2
   workup.STIRRINGthe reaction stirred at this temperature for 4 hours
3. 3
   温度warmed to 0° C
4. 4
   抽出The aqueous mixture was extracted with diethyl ether
5. 5
   乾燥the organic solution dried with brine and over sodium sulfate
6. 6
   その他Evaporation of the solvent

実験手順

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

出典