SU404234A1 - - Google Patents
Info
- Publication number
- SU404234A1 SU404234A1 SU844183A SU844183A SU404234A1 SU 404234 A1 SU404234 A1 SU 404234A1 SU 844183 A SU844183 A SU 844183A SU 844183 A SU844183 A SU 844183A SU 404234 A1 SU404234 A1 SU 404234A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methoxy
- mixture
- ethylenedioxy
- methylestra
- trien
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- DNAYTCUJACDUSG-XEYPJELSSA-N (8s,9s,13s,14s)-3-methoxy-9,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C[C@]2(C)C3=CC=C(OC)C=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C DNAYTCUJACDUSG-XEYPJELSSA-N 0.000 description 2
- CSATWFKFMCPGFD-VSLZGRPNSA-N 17-ethylenedioxy-3-methoxy-9α-methylestra-1,3,5(10)-triene Chemical compound C1C2OCCOC2[C@]2(C)[C@@H]1[C@@H]1CCC3=CC(OC)=CC=C3[C@@]1(C)CC2 CSATWFKFMCPGFD-VSLZGRPNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCJSGPWZKPHCSF-XPLLGQPASA-N 17-ethylenedioxy-3-methoxyestra-1,3,5(10)-trien-11-one Chemical compound C1C2OCCOC2[C@](CC2=O)(C)[C@@H]1[C@H]1[C@H]2C2=CC=C(OC)C=C2CC1 SCJSGPWZKPHCSF-XPLLGQPASA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- -1 steroid ketones Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU404234A1 true SU404234A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| SU403170A1 SU403170A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Findlay | Concerning 2-carbomethoxytropinone | |
| CH616161A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| SU404234A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH05112525A (ja) | ４−ヒドロキシ−２−オキソ−ピロリジン−１−イル−アセトアミドの製造方法 | |
| FR2523977A1 (fr) | Procede et composes intermediaires cles pour la preparation de la 19-norandrostenedione | |
| KR100268545B1 (ko) | 벤조페논 유도체의 제조방법 | |
| JPH10265441A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4145346A (en) | Preparation of 3β-hydroxy-27-norcholest-5-ene-25-one and intermediates thereof | |
| RU2204564C2 (ru) | Способ получения производного дезоксиуридина | |
| Strunz et al. | An improved procedure for the conversion of certain coumarins to 2, 2-dimethylchromenes: efficient transformation of umbelliferone to precocene 1 | |
| CN101508685A (zh) | 马来酸桂哌齐特的改进制备方法 | |
| SU403170A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP1466884A1 (fr) | Procédé de préparation du resvératrol et ses applications | |
| SU266653A1 (ru) | Пхнйпш-ая '^библиотека | |
| US4162364A (en) | Process for the preparation of 2-(3-benzoylphenyl)-propionic acid | |
| Kawase et al. | The Synthesis of 4′, 5, 7-Trihydroxy-8-methoxyisoflavone | |
| SU523642A3 (ru) | Способ получени производных трифенилфосфина | |
| JPH07267986A (ja) | ５α−コレスタ−８（１４）−エン−３β−オール−１５−オンおよび他の１５−酸素化ステロールの合成のための改良方法 | |
| US4220794A (en) | Synthetic intermediates for the preparation of diaromatic O-(amino-alkyl)oximes | |
| US3703530A (en) | Alkyl - 2 - alkyl - 2,3 - dicarboxy-5-norbornene - 7-acetate intermediates for the total synthesis of elenolic acids and analogs thereof | |
| SU339044A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ СТЕРОИДОВс АРОЛи | |
| JPH0119371B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS61246176A (ja) | アミノラクトンの調製方法 | |
| SU238445A1 (ru) | Спосоп получения производных просциляридина | |
| SU404238A1 (ru) | Способ получения флавон-7-оксиацетата низшего ал кила |