89968-59-2

Basic information

• Product Name: 10-Undecenoic acid, 2-(methyldiphenylsilyl)-, ethyl ester
• CAS NO: 89968-59-2
• Molecular Formula: C26H36O2Si
• Molecular Weight: 408.656
• Mol File: 89968-59-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 10-Undecenoic acid, 2-(methyldiphenylsilyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Undecenoic acid, 2-(methyldiphenylsilyl)-, ethyl ester(89968-59-2)
• EPA Substance Registry System: 10-Undecenoic acid, 2-(methyldiphenylsilyl)-, ethyl ester(89968-59-2)

Safety Data

• Hazardous Substances Data: 89968-59-2(Hazardous Substances Data)

Upstream product

• 692-86-4 ethyl 10-undecenenoate 
• 144-79-6 chloromethyldiphenylsilane 

Downstream Products

• 13688-67-0 1,10-undecadiene 
• 112197-28-1 2-Methyl-2-(methyl-diphenyl-silanyl)-undec-10-enoic acid ethyl ester 

Relevant articles and documents

Methyldiphenylsilylation of Ester and Lactone Enolates

The reactions of a variety of ester and lactone enolates with methyldiphenylchlorosilane were studied.The C-versus O-silylation, leading to the α-silyl ester or lactone and silyl ketene acetal, respectively, was studied as a function of the structure of the ester or lactone and the reaction conditions.It was found that all simple acetates are C-silylated irrespective of the steric demands of the alcohol portion of the ester.Esters that are monosubstituted in the α-position are cleanly C-silylated with the notable exceptions of ethyl phenylacetate and ethyl phenoxyacetate, both of which give mixtures of C- and O-silylation.The α,α-disubstituted esters give only O-silylation, but the α,α-substituted α-silyl esters are readily prepared by the alkylation of the appropriate monosubstituted α-silylated ester.The reaction of the lithium enolate of ethyl acetate and tert-butyl acetate with (S)-(-)-1-naphthylphenylmethylchlorosilane showed the reaction to occur with inversion of configuration at silicon.Methylation of tert-butyl (1-naphthylphenylmethylsilyl)acetate gave a 91:9 mixture of diastereomeric α-silyl propionates, which could not be separated.It was found that only the γ-lactones gave C-silylation with δ-valerolactone and ε-caprolactone giving O-silylation.

A SILICON MEDIATED CONVERSION OF ESTERS TO TERMINAL OLEFINS AND SPECIFICALLY DEUTERATED OLEFINS

-