- METHOD FOR PRODUCING 1,2,2,2-TETRAFLUORO-ETHYL DIFLUOROMETHYL ETHER (DESFLURANE)
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PROBLEM TO BE SOLVED: To provide a method for efficiently producing 1,2,2,2-tetrafluoro-ethyl difluoromethyl ether (desflurane), which is useful as an inhalation anesthetic, on an industrial scale. SOLUTION: By reacting hydrogen fluoride and trimethyl orthoformate to an equivalent (hemiacetal) of fluoral synthesized by hydrogenation reaction of methyl trifluoroacetate in the presence of a ruthenium catalyst, it can easily be converted to 1,2,2,2-tetrafluoro-ethyl methyl ether which is a synthetic intermediate of desflurane. The resulting 1,2,2,2-tetrafluoro-ethyl methyl ether can efficiently be derived to desflurane by chlorination followed by fluorination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0134; 0135
(2019/02/02)
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- MANUFACTURING METHOD OF α-FLUOROALDEHYDE EQUIVALENT
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PROBLEM TO BE SOLVED: To provide an industrial manufacturing method of α-fluoroaldehyde equivalent having industrial superiority. SOLUTION: α-fluoroaldehyde silylacetals are obtained by reacting an α-fluorocarboxylic acid derivative represented by the general formula, where R1 and R2 are each independently a hydrogen, a halogen atom, an alkyl group, a substituted alkyl group, an aromatic ring group or a substitute aromatic ring group, R3 represents a hydrogen atom, an alkyl group or a substitute alkyl group or R1, R2 and R3 may be same aliphatic ring or one constituting a part of an aliphatic heterocyclic ring, with a hydrogenated silicon compound in a presence of a Lewis acid compound. α-fluoroaldehyde equivalent can be derived by desilylation reaction on the resulting α-fluoroaldehyde silyl acetals. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0154-0157
(2016/12/12)
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- PROCESS FOR PRODUCING A-FLUOROALDEHYDES
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A production process of an α-fluoroaldehyde according to the present invention includes reaction of an α-fluoroester with hydrogen gas (H2) in the presence of a ruthenium complex. It is possible in the present invention to allow relatively easy industrial production of the α-fluoroaldehyde and to directly obtain, as stable synthetic equivalents of the α-fluoroaldehyde, not only a hydrate (as obtained by conventional techniques) but also a hemiacetal that is easy to purify and is of high value in synthetic applications. The present invention provides solutions to all problems in the conventional techniques and establishes the significantly useful process for production of the α-fluoroaldehyde.
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Paragraph 0059
(2014/06/24)
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- Taming of fluoroform: Direct nucleophilic trifluoromethylation of Si, B, S, and C centers
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Fluoroform (CF3H), a large-volume by-product of the manufacture of Teflon, refrigerants, polyvinylidene fluoride (PVDF), fire-extinguishing agents, and foams, is a potent and stable greenhouse gas that has found little practical use despite the growing importance of trifluoromethyl (CF3) functionality in more structurally elaborate pharmaceuticals, agrochemicals, and materials. Direct nucleophilic trifluoromethylation using CF3H has been a challenge. Here, we report on a direct trifluoromethylation protocol using close to stoichiometric amounts of CF3H in common organic solvents such as tetrahydrofuran (THF), diethyl ether, and toluene. The methodology is widely applicable to a variety of silicon, boron, and sulfur-based electrophiles, as well as carbon-based electrophiles.
- Surya Prakash,Jog, Parag V.,Batamack, Patrice T. D.,Olah, George A.
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p. 1324 - 1327
(2013/02/22)
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- The asymmetric synthesis of CF3- or -CF2-substituted tetrahydroquinolines by employing a chiral phosphoric acid as catalyst
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CF3- or -CF2-containing tetrahydroquinolines have been asymmetrically synthesized from the reaction of fluorinated N-arylimines with benzyl N-vinylcarbamate in the presence of a chiral phosphoric acid.
- Lin, Jin-Hong,Zong, Guoqiang,Du, Ruo-Bing,Xiao, Ji-Chang,Liu, Shubin
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supporting information; experimental part
p. 7738 - 7740
(2012/09/07)
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- The asymmetric Friedel-Crafts reaction of indoles with fluoroalkylated nitroalkenes catalyzed by chiral phosphoric acid
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The enantioselective Friedel-Crafts fluoroalkylation of indoles with fluoroalkylated nitroalkenes, catalyzed by chiral phosphoric acid is described. The regioselectivity of fluoroalkylated nitroalkenes is a problem worth discussing, and it was found that the carbon atom adjacent to the fluoroalkyl group is more reactive than that adjacent to NO2 group.
- Lin, Jin-Hong,Xiao, Ji-Chang
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experimental part
p. 4536 - 4539
(2011/10/09)
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- Highly diastereo- and enantioselective vinylogous Mannich reactions of fluorinated aldimines with siloxyfurans
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A highly regio- and enantioselective asymmetric vinylogous Mannich reaction of readily available fluorinated aldimines bearing a chiral auxiliary [(S)-1-phenylethyl group] with siloxyfurans to afford chiral fluorine-containing γ-butenolide or γ-lactone derivatives has been developed in the presence of silver acetate (10 mol%) and axially chiral phosphine-oxazoline ligand L1 (11 mol%). In most cases, the corresponding fluorinated adducts were obtained in high yields, good to excellent enantiomeric excesses and up to > 20:1 dr.
- Zhao, Qian-Yi,Yuan, Zhi-Liang,Shia, Min
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supporting information; experimental part
p. 637 - 643
(2011/04/25)
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- Interactive n→σ* delocalizations that control an aqueous organic equilibrium
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Hydrated acetaldehydes were condensed in D2O with substituted alcohols and thiols to determine ΔG of hemiacetalization by 1H NMR. Specific n→σ* delocalizalions in the alkoxy/alkylthio functionality of the product interact to influence n→σ* delocalization in the hemiacetal functionality. Delocalization in the latter functionality controls ΔG.
- Fan, Yun-Hua,Haseltine, John
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p. 9279 - 9282
(2007/10/03)
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- Zinc bromide promoted allylation of aluminum acetals derived from perfluoro carboxylic acid esters and diisobutylaluminum hydride. New convenient access to α-perfluoroalkylated homoallyl alcohols
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The reaction of aluminum acetals, generated in situ by the reduction between perfluoro carboxylic acid esters and diisobutylaluminum hydride, with a variety of allylstannanes efficiently proceeds in the presence of zinc bromide at 40°C to afford the corresponding α-perfluoroalkyl-substituted homoallyl alcohols in good yields.
- Ishihara,Hayashi,Yamanaka
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p. 5777 - 5780
(2007/10/02)
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