反应 #9769

反应方程式

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

溶剂

tetrahydrofuran

—

hexanes

反应条件

后处理

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
   萃取The aqueous mixture was extracted with diethyl ether
5. 5
   干燥the organic solution dried with brine and over sodium sulfate
6. 6
   其他Evaporation of the solvent

实验过程

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

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