Acylation of ester silyl enol ethers with acid chlorides
halides to the silyllithium reagent prior to reaction with acyl halides leads to This availability of the silyl enol ethers of acylsilanes as primary. handles than their ester and acid chloride counterparts. To the amides and cyclic silyl enol ethers notably allowed the synthesis. Catalytic Enantioselective Alkylation of Dioxanone Silyl Enol Ethers to Form. Tertiary Ethersi. Due to the difficult synthesis of β-ketoester starting. DISTANCE BETWEEN OOTY AND COORG PLACES
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Acylation of ester silyl enol ethers with acid chlorides forex earning tipsAcid chloride to ester example
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Zinc Chloride. Zinc chloride was dried by refluxing in thionyl chloride until gas evolution ceased. After the removal of the excess thionyl chloride the zinc chloride was stored in a desicator over KOH for 12 h. Antimony Trichloride. Antimony trichloride was sublimed [60"C Acylation of Ketone Silyl Enol Ethers. Procedure A. A mL flask with a septum inlet and magnetic stir bar was flame dried and flushed with argon. Zinc chloride 0. The flask was removed from the glovebag and connected to a mercury bubbler.
This was followed by the introduction of 5. After the flask was cooled to 0 "C, the acid chloride 5. After being stirred 1h at 0 "C, the reaction mixture was allowed to warm to room temperature and was quenched with approximately 10 mL of water. The layers were separated, and the aqueous layer was washed with methylene chloride.
The methylene chloride layers were combined and washed with a saturated sodium hydrogen carbonate solution. The organic extract was dried over sodium sulfate and analyzed by GC for C- and 0acylated ketone. Pure samples of product were obtained for spectral analysis by preparative GC.
Procedure B. Antimony trichloride 1. Methylene chloride 5. The acid chloride 5. After the mixture was stirred 1 h at 0 "C, the flask was warmed to room temperature, and the reaction was quenched with approximately 10 mL of HzO. The method for the work up was as described for procedure A above.
Spectral analyses of all products were performed on pure samples obtained by preparative GC. Enol esters obtained by 0-acylation were identified by their mass and 'H NMR spectra. GC analysis of the crude product after workup showed four components with the following identities and retention times: cyclohexanone 1. Spectral 9 Pray, A. GC analysis of the crude product shows four components [component identity retention time ]: cyclopentanone 1min , cyclopentanone enol acetate 1.
Cyclopentanone enol acetate was isolated from the reaction of cyclopentanone trimethylsilyl enol ether and acetyl chloride: 'H NMR CDCl, 5. The crude product was subjected to GC analysis which showed a four-component mixture [identity retention time ]: diethyl ketone 0. GC analysis of the crude product showed a four-component mixture [identity retention time ]: diisopropyl ketone 0. GC analysis of the crude product mixture showed five components [identity retention time ]: acetophenone 1.
GC analysis of the crude product identified four major components [identity retention time ]: isobutyrophenone 2. Spectral analysis of l-phenyl-2,2-dimethyl-l,3-butanedione gave the following: 'H NMR 1. GC analysis of the crude product showed three major components [identity retention time ]: diethyl ketone enol 11 Tavernia, D. A,; Strom, E. GC analysis of the crude product identified three components [identity retention time ]: diethyl ketone enol 3.
GC analysis of the crude products showed four components [identity retention time ]: diethyl ketone 0. GC analysis of the crude product showed four major componenta [identity retention time ]: diethyl ketone 1. The silyl enol ethers could be hydrolysed to acyl silanes by treatment with acid.
The alcohols were prepared in reasonable yields by hydrolysis of the bis trimethylsilyl carbinol silyl ethers 94,95, which in turn were produced from the corresponding esters using another silyl acyloin reaction , which itself, ironically, proceeds through an acyl silane intermediate Scheme 21 In this procedure it is the Z isomer which is the predominant product Scheme 24 Hydrolysis to the acyl silanes was achieved using hydrochloric acid -acetone.
This has been achieved with the silyl enol ethers using bromine at low temperatures, but the reaction suffers from the general Addition of phenyl sulphenyl chloride to the silyl enol ether with subsequent elimination of chlorotrimethylsilane gives the a- phenylthio acyl silane. Oxidation to the sulphoxide followed by in situ elimination of benzenesulphenic For example, when aroyl silanes were treated with a Wittig reagent , none of the expected alkenes was obtained, and the only reaction products isolated were silyl enol ether and triphenylphosphine Scheme 73 , When alkanoyl silanes were treated with Wittig reagents , however, only the normal olefinated vinyl silane products were isolated Scheme 74 Under soluble lithium salt conditions , Z- vinyl silanes were produced with very high selectivities the reaction was used to prepare a pheromone component 50 of the sweet potato leaf folder moth Scheme 75
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