77772-22-6

Usage

Uses

Used in Chemical Synthesis:
Propanoic acid, 2-(methyldiphenylsilyl)-, ethyl ester is used as a precursor for the synthesis of 1,1-disubstituted 1-propenes. Its unique structure allows for the formation of these valuable compounds, which can be further utilized in various chemical reactions and applications.
Used in Organic Chemistry:
As a reagent, Propanoic acid, 2-(methyldiphenylsilyl)-, ethyl ester is used in the synthesis of α-methyl-α,β-unsaturated esters. These esters are important intermediates in the production of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Production of 2-(methyldiphenylsilyl)-3-alkanones:
Propanoic acid, 2-(methyldiphenylsilyl)-, ethyl ester reacts with primary Grignard reagents to produce 2-(methyldiphenylsilyl)-3-alkanones. These alkanones are key intermediates in the synthesis of various organic compounds, including pharmaceuticals and other specialty chemicals.
Used in the Synthesis of Methyldiphenylsilyl Enol Ethers:
The reaction of Propanoic acid, 2-(methyldiphenylsilyl)-, ethyl ester with primary Grignard reagents can also lead to the formation of regioselectively derived methyldiphenylsilyl enol ethers. These enol ethers are valuable synthetic intermediates in organic chemistry, with applications in the synthesis of various complex molecules and pharmaceuticals.

Preparation

whereas the direct silylation of the lithium enolate of an ester normally results in the formation of a mixture of the α-silyl ester and the corresponding silyl ketene acetal, the reaction of lithium ester enolates with methyldiphenylchlorosilane gives exclusively the α-methyldiphenylsilyl ester. This direct C-silylation is the best general route to α-silyl esters.

Upstream product

• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 13107-13-6 methyldiphenylvinylsilane 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 6111-99-5 ethyl diazoalaninate 
• 776-76-1 methyldiphenylsilane 
• 144-79-6 chloromethyldiphenylsilane 
• 105-37-3 Ethyl propionate 

Downstream Products

• 63963-01-9 ethyl 2-cyclohexilidenepropionate 
• 99165-52-3 4-methyl-4-(diphenylmethylsilyl)-1,8-nonadien-5-one 
• 40558-71-2 1,1-Dibenzylpropene 
• 7042-33-3 ethyl (E)-2-methyl-3-phenyl-2-propenoate 
• 7042-34-4 ethyl c-α–methylcinnamate 
• 21016-46-6 2,4-dimethyl-pent-2-enioc acid ethyl ester 
• 21016-47-7 ethyl (Z)-2,4-dimethylpent-2-enoate 

Relevant academic research and scientific papers

Iron-Catalyzed Carbene Insertion Reactions of α-Diazoesters into Si-H Bonds

An efficient iron-catalyzed carbene insertion reaction of α-diazo carbonyl compounds into the Si-H bond was developed. A wide range of α-silylesters was obtained in high yields (up to 99%) from α-diazoesters using a simple iron(II) salt as catalyst.

The Highly Regioselective Carbonylation of Vinylsilanes

The hydroesterification of vinylsilanes, catalyzed by transition-metal complexes, afforded both β-silyl esters 2 and α-silyl esters 3 in high yield.The Pd(II) complex-catalyzed reaction showed high β-regioselectivity, whereas the Co2(CO)8-catalyzed reaction showed high α-regioselectivity.Vinylsilanes which bore trialkyl-, diphenylmethyl-, dimethylethoxy-, trimethoxy-, diphenylfluoro-, and difluorophenylsilyl groups were regioselectively, and in some cases regiospecifically, hydroesterified.Pd(II) complexes were also shown to be effective catalysts of the hydrocarboxylation of vinylsilanes.Hydrocarboxylation was β-regiospecific and gave excellent yields of β-silyl carboxylic acids.Reasonable mechanisms for the reactions are described.

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.

Reaction of α-Silyl Esters with Grignard Reagents: A Synthesis of β-Keto Silanes and Ketones. Preparation of the Douglas Fir Tussock Moth Pheromone

A variety of α-diphenylmethylsilyl esters have been prepared and reacted with Grignard reagents.The reaction is relatively slow in refluxing THF and can be controlled to allow the addition of 1 equiv of the Grignard reagent, providing the corresponding β-keto silane.Protiodesilylation of the β-keto silane results in the overall conversion of an ester to a ketone.This ester to ketone methodology has been applied to a two-step synthesis of the pheromone of the Douglas fir tussock moth.The β-keto silanes are viable precursors to regioselectively generated enol silyl ethers.The reaction of ethyl 2-methyl-2-(diphenylmethylsilyl)propionate with vinylmagnesium bromide or 2-methyl 1-propenylmagnesium bromide results in the addition of 2 equiv of the Grignard reagent, the second in a Michael fashion.