Reaktion #9769

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

—

hexanes

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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

Quelle