JPH0586770B2 - - Google Patents
Info
- Publication number
- JPH0586770B2 JPH0586770B2 JP4845386A JP4845386A JPH0586770B2 JP H0586770 B2 JPH0586770 B2 JP H0586770B2 JP 4845386 A JP4845386 A JP 4845386A JP 4845386 A JP4845386 A JP 4845386A JP H0586770 B2 JPH0586770 B2 JP H0586770B2
- Authority
- JP
- Japan
- Prior art keywords
- salt
- anion
- sodium salt
- chem
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 fluorine organic compound Chemical class 0.000 claims description 58
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UWDCUCCPBLHLTI-UHFFFAOYSA-N 1-fluoropyridin-1-ium Chemical class F[N+]1=CC=CC=C1 UWDCUCCPBLHLTI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- IEARPTNIYZTWOZ-UHFFFAOYSA-N ethene Chemical compound [CH-]=C IEARPTNIYZTWOZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000003682 fluorination reaction Methods 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 235000013024 sodium fluoride Nutrition 0.000 description 3
- 239000011775 sodium fluoride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BANWBNLRSDINSG-UHFFFAOYSA-N 1-fluoropyridin-2-one Chemical compound FN1C=CC=CC1=O BANWBNLRSDINSG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UOWIYNWMROWVDG-UHFFFAOYSA-N 1-dimethoxyphosphorylpropan-2-one Chemical compound COP(=O)(OC)CC(C)=O UOWIYNWMROWVDG-UHFFFAOYSA-N 0.000 description 1
- PRIGFEJKMMRJSF-UHFFFAOYSA-M 1-fluoro-2,4,6-trimethylpyridin-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=CC(C)=[N+](F)C(C)=C1 PRIGFEJKMMRJSF-UHFFFAOYSA-M 0.000 description 1
- JFZMMCYRTJBQQI-UHFFFAOYSA-M 1-fluoropyridin-1-ium;trifluoromethanesulfonate Chemical compound F[N+]1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F JFZMMCYRTJBQQI-UHFFFAOYSA-M 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XYNQJEDEUVQGLP-UHFFFAOYSA-N C(C)(=O)O.C(CCC)[Li] Chemical compound C(C)(=O)O.C(CCC)[Li] XYNQJEDEUVQGLP-UHFFFAOYSA-N 0.000 description 1
- DATDZAZLXPKXBF-UHFFFAOYSA-L C(CC(=O)[O-])(=O)[O-].C(C)C([N+](C)(C)C)CC.C(C)C(CC)[N+](C)(C)C Chemical compound C(CC(=O)[O-])(=O)[O-].C(C)C([N+](C)(C)C)CC.C(C)C(CC)[N+](C)(C)C DATDZAZLXPKXBF-UHFFFAOYSA-L 0.000 description 1
- QXJAACKBSCULPH-UHFFFAOYSA-N C=1C=CC=CC=1[Mg]C1=CC=CC=C1 Chemical class C=1C=CC=CC=1[Mg]C1=CC=CC=C1 QXJAACKBSCULPH-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- CKCYDFVZAPRMBQ-UHFFFAOYSA-M [Cl-].CCCCCCCCCC[Mg+] Chemical compound [Cl-].CCCCCCCCCC[Mg+] CKCYDFVZAPRMBQ-UHFFFAOYSA-M 0.000 description 1
- WGZLJRBPCAVYPR-UHFFFAOYSA-N [Li].C#CC1=CC=CC=C1 Chemical compound [Li].C#CC1=CC=CC=C1 WGZLJRBPCAVYPR-UHFFFAOYSA-N 0.000 description 1
- SHZBRYQYYSXMPN-UHFFFAOYSA-N [N+](=O)([O-])C(C)[N+](=O)[O-].[Na] Chemical compound [N+](=O)([O-])C(C)[N+](=O)[O-].[Na] SHZBRYQYYSXMPN-UHFFFAOYSA-N 0.000 description 1
- CJKOYHIJFXXCBB-UHFFFAOYSA-N [N+](=O)([O-])CC.[Na] Chemical compound [N+](=O)([O-])CC.[Na] CJKOYHIJFXXCBB-UHFFFAOYSA-N 0.000 description 1
- DHFOXWHMSQRJBS-UHFFFAOYSA-N [N+](=O)([O-])C[N+](=O)[O-].[Na] Chemical compound [N+](=O)([O-])C[N+](=O)[O-].[Na] DHFOXWHMSQRJBS-UHFFFAOYSA-N 0.000 description 1
- QFHUXXJLWQEQEU-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)C#C Chemical compound [Na].C1(=CC=CC=C1)C#C QFHUXXJLWQEQEU-UHFFFAOYSA-N 0.000 description 1
- XHRNWLQQVSYTDD-UHFFFAOYSA-N [Na].C[N+]([O-])=O Chemical compound [Na].C[N+]([O-])=O XHRNWLQQVSYTDD-UHFFFAOYSA-N 0.000 description 1
- RAFKCLFWELPONH-UHFFFAOYSA-N acetonitrile;dichloromethane Chemical compound CC#N.ClCCl RAFKCLFWELPONH-UHFFFAOYSA-N 0.000 description 1
- 150000000476 acetylides Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KYIBHFNJISEQRB-UHFFFAOYSA-N cyclohexane-1,3-dione;sodium Chemical compound [Na].O=C1CCCC(=O)C1 KYIBHFNJISEQRB-UHFFFAOYSA-N 0.000 description 1
- QZVPJZDHSABXOZ-UHFFFAOYSA-N cyclopentane-1,3-dione;sodium Chemical compound [Na].O=C1CCC(=O)C1 QZVPJZDHSABXOZ-UHFFFAOYSA-N 0.000 description 1
- HCDITHVDEPPNIL-UHFFFAOYSA-L dipotassium;propanedioate Chemical compound [K+].[K+].[O-]C(=O)CC([O-])=O HCDITHVDEPPNIL-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PTZFYJUFLYSVIV-UHFFFAOYSA-N ethyl 1-fluoro-2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1(F)CCCC1=O PTZFYJUFLYSVIV-UHFFFAOYSA-N 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- AXCBHWGTRNNXKG-UHFFFAOYSA-N fluorochlorane oxide Chemical compound FCl=O AXCBHWGTRNNXKG-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- XHEHDQPARIPMRX-UHFFFAOYSA-N lithium;dioxido(propan-2-ylidene)azanium Chemical compound [Li+].CC(C)=[N+]([O-])[O-] XHEHDQPARIPMRX-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
- OFUICLLNJWZMHW-UHFFFAOYSA-M magnesium;ethenylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH-]=CC1=CC=CC=C1 OFUICLLNJWZMHW-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- CYSFUFRXDOAOMP-UHFFFAOYSA-M magnesium;prop-1-ene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C=C CYSFUFRXDOAOMP-UHFFFAOYSA-M 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- HZOAWXQTMQXJBS-UHFFFAOYSA-N methyl 2-cyanoacetate;sodium Chemical compound [Na].COC(=O)CC#N HZOAWXQTMQXJBS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- ZWNKCUAWCADLQC-UHFFFAOYSA-N pentane-2,4-dione;potassium Chemical compound [K].CC(=O)CC(C)=O ZWNKCUAWCADLQC-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- YPPQYORGOMWNMX-UHFFFAOYSA-L sodium phosphonate pentahydrate Chemical compound [Na+].[Na+].[O-]P([O-])=O YPPQYORGOMWNMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- UAKCMIIOSJFOTD-UHFFFAOYSA-M sodium;3-oxobutanoate Chemical compound [Na+].CC(=O)CC([O-])=O UAKCMIIOSJFOTD-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4845386A JPS62207230A (ja) | 1986-03-07 | 1986-03-07 | 含フツ素有機化合物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4845386A JPS62207230A (ja) | 1986-03-07 | 1986-03-07 | 含フツ素有機化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62207230A JPS62207230A (ja) | 1987-09-11 |
| JPH0586770B2 true JPH0586770B2 (en, 2012) | 1993-12-14 |
Family
ID=12803766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4845386A Granted JPS62207230A (ja) | 1986-03-07 | 1986-03-07 | 含フツ素有機化合物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62207230A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02290884A (ja) * | 1989-04-28 | 1990-11-30 | Rikagaku Kenkyusho | 有機けい素化合物の製造方法 |
| JPH07233097A (ja) * | 1994-02-23 | 1995-09-05 | Chichibu Onoda Cement Corp | 親電子型フッ素化剤の製造方法 |
-
1986
- 1986-03-07 JP JP4845386A patent/JPS62207230A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62207230A (ja) | 1987-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4578503A (en) | Alkylated or alkenylated malonic acid or its derivatives having a fluorine | |
| JPS6145617B2 (en, 2012) | ||
| JP2000500480A (ja) | ペルフルオロアルキル化に使用する方法及びこの方法に使用する反応物 | |
| JPH0586770B2 (en, 2012) | ||
| JP2003335735A (ja) | パーフルオロイソプロピルアニリン類の製造方法 | |
| Corey et al. | New precursors to silafluorenes | |
| JP4523324B2 (ja) | ペルフルオロアルキル基を有するアルコール誘導体の製造方法 | |
| JP2000095730A (ja) | ハロゲン化フェニルマロン酸エステルの製造方法 | |
| JP2001114756A (ja) | β−カロチンの製造方法 | |
| EP0154894B1 (en) | A sulfur-containing fluorinated unsaturated compound and its manufacturing process | |
| JP4034040B2 (ja) | 含フッ素ジエン化合物 | |
| EP0005280B1 (en) | A process for the reduction of carboxylic acid halides to corresponding aldehydes | |
| JPH10130178A (ja) | ｇｅｍ−ジフルオロオレフィン類の製造方法、同製造方法に用いるジルコノセン、及びその製造方法 | |
| JP2001322950A (ja) | ２−アルキレンアダマンタンの製造方法 | |
| JP3044898B2 (ja) | フランカルビノール誘導体の製造方法 | |
| FR2604703A1 (fr) | Procede de preparation de polyfluoroenolates | |
| JPH0586768B2 (en, 2012) | ||
| Narske | Stereoselective synthesis of substituted (E) and (Z)-difluoroethenyl derivatives | |
| JPH08231526A (ja) | フルオロラクトン化合物及びその製造方法 | |
| JPH06157381A (ja) | ポリフルオロエノラートの製造法 | |
| JPH0150210B2 (en, 2012) | ||
| JPH0653698B2 (ja) | １−（３−フエノキシフエニル）−４−（４−アルコキシフエニル）−４−メチルペンタン誘導体の製造方法 | |
| JPH029856A (ja) | 新規なヒドロキシスルホンおよびその製造方法 | |
| JPS62212347A (ja) | シス−１１−テトラデセニルアセテ−トの製造方法 | |
| JPH0319216B2 (en, 2012) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |