CA1052801A - Tetrahydrofurane derivatives and production thereof - Google Patents
Tetrahydrofurane derivatives and production thereofInfo
- Publication number
- CA1052801A CA1052801A CA202,705A CA202705A CA1052801A CA 1052801 A CA1052801 A CA 1052801A CA 202705 A CA202705 A CA 202705A CA 1052801 A CA1052801 A CA 1052801A
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydro
- furyl
- prepared
- octanoic acid
- product obtained
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000007984 tetrahydrofuranes Chemical class 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZJTPMIDURCBBTK-UHFFFAOYSA-N methyl 8-(5-formyloxolan-2-yl)octanoate Chemical compound COC(=O)CCCCCCCC1CCC(C=O)O1 ZJTPMIDURCBBTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- -1 sodium tetrahydroborate Chemical compound 0.000 claims description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical compound CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 claims description 2
- WLVPTOUKKHEHCW-UHFFFAOYSA-N 8-[5-(3-hydroxyoctyl)oxolan-2-yl]octanoic acid Chemical compound CCCCCC(O)CCC1CCC(CCCCCCCC(O)=O)O1 WLVPTOUKKHEHCW-UHFFFAOYSA-N 0.000 claims description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 2
- 238000003747 Grignard reaction Methods 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 2
- VACWJQFINOBGIO-UHFFFAOYSA-N methyl 8-[5-(3-oxooctyl)oxolan-2-yl]octanoate Chemical compound CCCCCC(=O)CCC1CCC(CCCCCCCC(=O)OC)O1 VACWJQFINOBGIO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 22
- 239000000126 substance Substances 0.000 claims 10
- DOKQYJICSHTGHM-UHFFFAOYSA-N 8-[5-(3-hydroxyoct-1-enyl)oxolan-2-yl]octanoic acid Chemical compound CCCCCC(O)C=CC1CCC(CCCCCCCC(O)=O)O1 DOKQYJICSHTGHM-UHFFFAOYSA-N 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- HJPCYQFRJQEXSL-UHFFFAOYSA-N chloro(trichloromethyl)silane Chemical compound Cl[SiH2]C(Cl)(Cl)Cl HJPCYQFRJQEXSL-UHFFFAOYSA-N 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- JXZCSLDZDSSKRV-UHFFFAOYSA-N methyl 8-[5-(3-hydroxyoct-1-enyl)oxolan-2-yl]octanoate Chemical compound CCCCCC(O)C=CC1CCC(CCCCCCCC(=O)OC)O1 JXZCSLDZDSSKRV-UHFFFAOYSA-N 0.000 claims 1
- CXGTYDZTZWZSQB-UHFFFAOYSA-N methyl 8-[5-(3-hydroxyoctyl)oxolan-2-yl]octanoate Chemical compound CCCCCC(O)CCC1CCC(CCCCCCCC(=O)OC)O1 CXGTYDZTZWZSQB-UHFFFAOYSA-N 0.000 claims 1
- YLRNWOXOUDDVBO-UHFFFAOYSA-N methyl 8-[5-(3-oxooct-1-enyl)oxolan-2-yl]octanoate Chemical compound CCCCCC(=O)C=CC1CCC(CCCCCCCC(=O)OC)O1 YLRNWOXOUDDVBO-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 239000003054 catalyst Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WALZTIHATHSJOA-UHFFFAOYSA-N 8-[5-(3-hydroxy-3-methyloctyl)oxolan-2-yl]octanoic acid Chemical compound CCCCCC(C)(O)CCC1CCC(CCCCCCCC(O)=O)O1 WALZTIHATHSJOA-UHFFFAOYSA-N 0.000 description 1
- GRXVHHIDPGNSGE-UHFFFAOYSA-N 8-[5-(3-oxooctyl)oxolan-2-yl]octanoic acid Chemical compound CCCCCC(=O)CCC1CCC(CCCCCCCC(O)=O)O1 GRXVHHIDPGNSGE-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical compound COP(=O)OC HZCDANOFLILNSA-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
- 229930194542 Keto Natural products 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003529 luteolytic effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- KVERUONTDNOFQL-UHFFFAOYSA-N methyl 8-[5-(dimethoxymethyl)oxolan-2-yl]octanoate Chemical compound COC(OC)C1CCC(CCCCCCCC(=O)OC)O1 KVERUONTDNOFQL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium 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
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2924173A GB1466256A (en) | 1973-06-20 | 1973-06-20 | 2,5-substituted furans and their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052801A true CA1052801A (en) | 1979-04-17 |
Family
ID=10288383
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA202,705A Expired CA1052801A (en) | 1973-06-20 | 1974-06-18 | Tetrahydrofurane derivatives and production thereof |
| CA202,704A Expired CA1053686A (en) | 1973-06-20 | 1974-06-18 | Furane derivatives and production thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA202,704A Expired CA1053686A (en) | 1973-06-20 | 1974-06-18 | Furane derivatives and production thereof |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5032164A (enExample) |
| BE (2) | BE816569A (enExample) |
| CA (2) | CA1052801A (enExample) |
| DD (2) | DD113356A5 (enExample) |
| DE (2) | DE2429248A1 (enExample) |
| DK (2) | DK329674A (enExample) |
| FI (2) | FI187374A7 (enExample) |
| FR (2) | FR2234301B1 (enExample) |
| GB (1) | GB1466256A (enExample) |
| IL (2) | IL45065A (enExample) |
| NL (2) | NL7408199A (enExample) |
| NO (2) | NO742234L (enExample) |
| SE (2) | SE7408096L (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989005864A1 (en) * | 1987-12-15 | 1989-06-29 | The Trustees Of Princeton University | Transgenic testing systems for mutagens and carcinogens |
-
1973
- 1973-06-20 GB GB2924173A patent/GB1466256A/en not_active Expired
-
1974
- 1974-06-18 CA CA202,705A patent/CA1052801A/en not_active Expired
- 1974-06-18 CA CA202,704A patent/CA1053686A/en not_active Expired
- 1974-06-19 FR FR7421232A patent/FR2234301B1/fr not_active Expired
- 1974-06-19 JP JP49069266A patent/JPS5032164A/ja active Pending
- 1974-06-19 SE SE7408096A patent/SE7408096L/xx unknown
- 1974-06-19 BE BE145628A patent/BE816569A/xx unknown
- 1974-06-19 DD DD179283A patent/DD113356A5/xx unknown
- 1974-06-19 DD DD179281A patent/DD112755A5/xx unknown
- 1974-06-19 DE DE2429248A patent/DE2429248A1/de active Pending
- 1974-06-19 SE SE7408097A patent/SE7408097L/xx unknown
- 1974-06-19 FR FR7421231A patent/FR2234302B1/fr not_active Expired
- 1974-06-19 DE DE2429247A patent/DE2429247A1/de active Pending
- 1974-06-19 IL IL45065A patent/IL45065A/xx unknown
- 1974-06-19 BE BE145629A patent/BE816570A/xx unknown
- 1974-06-19 NL NL7408199A patent/NL7408199A/xx not_active Application Discontinuation
- 1974-06-19 FI FI1873/74A patent/FI187374A7/fi unknown
- 1974-06-19 NO NO742234A patent/NO742234L/no unknown
- 1974-06-19 IL IL45066A patent/IL45066A/en unknown
- 1974-06-19 NO NO742235A patent/NO742235L/no unknown
- 1974-06-19 FI FI1874/74A patent/FI187474A7/fi unknown
- 1974-06-19 NL NL7408200A patent/NL7408200A/xx not_active Application Discontinuation
- 1974-06-19 JP JP49069267A patent/JPS5032165A/ja active Pending
- 1974-06-20 DK DK329674A patent/DK329674A/da unknown
- 1974-06-20 DK DK329874A patent/DK329874A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7408199A (enExample) | 1974-12-24 |
| CA1053686A (en) | 1979-05-01 |
| NO742234L (enExample) | 1975-01-13 |
| NL7408200A (enExample) | 1974-12-24 |
| BE816570A (fr) | 1974-10-16 |
| DE2429247A1 (de) | 1975-01-16 |
| DK329874A (enExample) | 1975-02-10 |
| FR2234302B1 (enExample) | 1978-12-01 |
| IL45066A0 (en) | 1974-09-10 |
| FI187474A7 (enExample) | 1974-12-21 |
| JPS5032164A (enExample) | 1975-03-28 |
| DD112755A5 (enExample) | 1975-05-05 |
| DE2429248A1 (de) | 1975-01-16 |
| FR2234301B1 (enExample) | 1978-09-22 |
| DK329674A (enExample) | 1975-02-10 |
| FR2234302A1 (enExample) | 1975-01-17 |
| GB1466256A (en) | 1977-03-02 |
| IL45065A (en) | 1978-06-15 |
| DD113356A5 (enExample) | 1975-06-05 |
| SE7408097L (enExample) | 1974-12-23 |
| FR2234301A1 (enExample) | 1975-01-17 |
| IL45066A (en) | 1977-07-31 |
| BE816569A (fr) | 1974-10-16 |
| JPS5032165A (enExample) | 1975-03-28 |
| FI187374A7 (enExample) | 1974-12-21 |
| NO742235L (enExample) | 1975-01-13 |
| IL45065A0 (en) | 1974-09-10 |
| SE7408096L (enExample) | 1974-12-23 |
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