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ChemicalBook CAS DataBase List 1-METHYL-1-(TRIMETHYLSILYL)ALLENE
74542-82-8

1-METHYL-1-(TRIMETHYLSILYL)ALLENE synthesis

7synthesis methods
1-methyl-1-(trialkylsilyl)allenes can be conveniently prepared by the method of Vermeer. Silylsubstituted propargyl mesylates thus undergo SN2 displacement by the organocopper reagent generated from methylmagnesium chloride, copper(I) bromide, and lithium bromide 1-Methyl-1-(trimethylsilyl)allene is produced in 52% yield from commercially available (trimethylsilyl)propargyl alcohol in this fashion (eq 1). The t-butyldimethylsilyl and triisopropylsilyl analogs are synthesized by the same method in 90% and 58% yield, respectively. Propargyl alcohols bearing these and other trialkylsilyl groups can be prepared by treatment of propargyl alcohol with n-butyllithium and the appropriate trialkylsilyl chloride. Allenylsilanes bearing other C-1 substituents can be prepared in an analogous manner by using the appropriate Grignard reagents.

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Yield:74542-82-8 83%

Reaction Conditions:

with methanesulfonyl chloride;copper(I) bromide;lithium bromide in tetrahydrofuran at -70 - 25;

References:

Danheiser, Rick L.;Carini, David J.;Kwasigroch, Carrie A. [Journal of Organic Chemistry,1986,vol. 51,# 20,p. 3870 - 3878]

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