- Method for synthesizing 2-phenyl-2-trimethylsilyl acetyl chloride from trimethyl (vinyl) silane
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The invention relates to a method for synthesizing 2-phenyl-2-trimethylsilyl acetyl chloride from trimethyl (vinyl) silane, to mainly solve the technical problem that an industrial synthesis method ofthe compound is in shortage. The method comprises the following three steps: step 1, dissolving trimethyl(vinyl)silane in dichloromethane, and adding 3-chloroperoxybenzoic acid at a low temperature for reaction to obtain trimethyl (2-epoxyethyl)silane; step 2, dissolving phenyl magnesium bromide and cuprous cyanide in isopropyl ether at a low temperature, and adding trimethyl(2-epoxyethyl)silanefor reaction to generate 2-phenyl-2-trimethylsilyl ethanol; step 3, carrying out a reaction of a tetrahydrofuran solution of the 2-phenyl-2-trimethylsilyl ethanol under the condition with triethylamine and triphosgene to generate 2-phenyl-2-trimethylsilyl acetyl chloride.
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Paragraph 0008-0010
(2018/05/01)
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- The (2-phenyl-2-trimethylsiylyl)ethyl (PTMSE) ester - A carboxy protecting group cleavable under neutral conditions
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(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters of aminoacids and peptides are stable under the conditions of hydrogenolytic cleavage of benzoxycarbonyl(Z) and benzyl ester groups, base-induced removal of Fmoc groups, palladium(0)-catalyzed removal of allyloxycarbonyl (Aloc) and even acidolytic cleavage of Boc groups. PTMSE esters are also stable under the conditions of peptide condensation reactions. The PTMSE ester is selectively cleaved by treatment with tetrabutylammonium fluoride (TBAF) trihydrate in dichloromethane, i.e. under almost neutral conditions, within a few minutes and, therefore, considered a valuable novel carboxy protecting group.
- Wagner, Michael,Kunz, Horst
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p. 928 - 936
(2007/10/03)
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- (2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters - A novel carboxyl protecting group
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A novel silicon-containing protecting group based on the known 2- (trimethylsilyl)ethyl system has been developed for the protection of the carboxylic group, e.g. in peptide chemistry. The new protecting group can be cleaved by treatment with tetra-n-butylammonium fluoride much more rapidly than the known 2-(trimethylsilyl)ethyl group, leading to less side reactions.
- Wagner, Michael,Kunz, Horst
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p. 400 - 402
(2007/10/03)
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- The (2-phenyl-2-trimethylsilyl)ethoxycarbonyl (Psoc) group - A novel amino protecting group
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A novel silicon containing protecting group has been developed based on the known 2-(trimethylsilyl)ethyl system. The new protecting group is cleaved under very mild conditions by treatment with tetra-n-butylammonium fluoride in CH2Cl2 much more rapidly than the 2-(trimethylsilyl)ethoxycarbonyl group, leading to less side reactions.
- Wagner,Heiner,Kunz
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p. 1753 - 1756
(2007/10/03)
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- Silicon Effects. V. β-Silicon Effect in the Solvolysis of 2-Phenylethyl Compounds
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The rates of the solvolysis of 2-aryl-2-(trimethylsilyl)ethyl compounds, ArCH(SiMe3)CH2X (4: X=Cl and OCOCF3; Ar=C6H5 and p-MeOC6H4), have been measured in various solvents at 25 deg C.The solvolysis of the chloride, 4 (X=Cl; Ar=C6H5), exhibited an m valu
- Hayakawa, Fumie,Watanabe, Sin-ichiro,Shimizu, Nobujiro,Tsuno, Yuho
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p. 153 - 157
(2007/10/02)
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