BE572885A - - Google Patents

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Publication number

BE572885A

BE572885A BE572885DA BE572885A BE 572885 A BE572885 A BE 572885A BE 572885D A BE572885D A BE 572885DA BE 572885 A BE572885 A BE 572885A

Authority

BE

Belgium

Prior art keywords

ethylene

bis

ketal

dione

reacted

Prior art date

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• 150000001875 compounds Chemical class 0.000 claims description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
• 239000005977 Ethylene Substances 0.000 claims description 11
• 239000012448 Lithium borohydride Substances 0.000 claims description 6
• NZTNZPDOBQDOSO-UHFFFAOYSA-N lithium;boron(1-) Chemical compound [Li+].[B-] NZTNZPDOBQDOSO-UHFFFAOYSA-N 0.000 claims description 6
• SOWJCIWZEUNWJP-YDGRKWSBSA-N Br[C@H]1C([C@@H]2[C@]3(CCC(CC3CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@@]12C)=O)C)=O Chemical compound Br[C@H]1C([C@@H]2[C@]3(CCC(CC3CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@@]12C)=O)C)=O SOWJCIWZEUNWJP-YDGRKWSBSA-N 0.000 claims description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
• VBTQNRFWXBXZQR-UHFFFAOYSA-N N-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 4
• 239000002253 acid Substances 0.000 claims description 3
• 239000003377 acid catalyst Substances 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 238000000034 method Methods 0.000 claims 13
• DUHUCHOQIDJXAT-SWPDNEGGSA-N (3R,8S,9S,10S,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one Chemical compound C1CC2C[C@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O DUHUCHOQIDJXAT-SWPDNEGGSA-N 0.000 claims 2
• SRDFQHNJMGOFNH-HDJUTTSVSA-N Br[C@H]1C([C@@H]2[C@]3(CC[C@H](CC3CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@@]12C)O)C)=O Chemical compound Br[C@H]1C([C@@H]2[C@]3(CC[C@H](CC3CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@@]12C)O)C)=O SRDFQHNJMGOFNH-HDJUTTSVSA-N 0.000 claims 2
• 239000011260 aqueous acid Substances 0.000 claims 2
• CEBZORSAHLSRQW-PYASFRJRSA-N (8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C1CC2CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 CEBZORSAHLSRQW-PYASFRJRSA-N 0.000 claims 1
• BJQVYOSLJSLGJU-CVXUDELMSA-N C(C)(=O)O[C@H]1CC2CC[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4([C@H](C([C@@H]3[C@]2(CC1)C)=O)Br)C Chemical compound C(C)(=O)O[C@H]1CC2CC[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4([C@H](C([C@@H]3[C@]2(CC1)C)=O)Br)C BJQVYOSLJSLGJU-CVXUDELMSA-N 0.000 claims 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
• 229910052751 metal Inorganic materials 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
• 150000004692 metal hydroxides Chemical class 0.000 claims 1
• 230000001590 oxidative Effects 0.000 claims 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
• 238000001914 filtration Methods 0.000 description 7
• 229910052736 halogen Inorganic materials 0.000 description 7
• 150000002367 halogens Chemical group 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 229960000583 Acetic Acid Drugs 0.000 description 4
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• -1 steroid compounds Chemical class 0.000 description 3
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
• IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
• 230000003110 anti-inflammatory Effects 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
• WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
• YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-Sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
• XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
• 206010003246 Arthritis Diseases 0.000 description 1
• 230000002378 acidificating Effects 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000002026 chloroform extract Substances 0.000 description 1
• 229940117975 chromium trioxide Drugs 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 239000004744 fabric Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
• 230000003472 neutralizing Effects 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000002194 synthesizing Effects 0.000 description 1