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CAS No. : | 84646-68-4 | MDL No. : | MFCD00154460 |
Formula : | C9H12O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PQMIUYZOJQILOZ-UHFFFAOYSA-N |
M.W : | 184.19 | Pubchem ID : | 699253 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With bis(cyclopentadienyl)titanium (III) chloride; cyclohexa-1,4-diene In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In dichloromethane at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: formaldehyd; Dimethyl 3-cyclopentene-1,1-dicarboxylate With sulfuric acid; acetic acid at 60℃; for 24h; Stage #2: With chloro-trimethyl-silane In methanol Stage #3: With Pancreatin | |
Stage #1: formaldehyd; Dimethyl 3-cyclopentene-1,1-dicarboxylate With sulfuric acid; acetic acid Stage #2: With chloro-trimethyl-silane In methanol Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium hydroxide In methanol at 20℃; for 20h; | |
11.48 g | With water; potassium hydroxide In tetrahydrofuran at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 4h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 20℃; | |
87% | Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | |
84% | Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 25℃; for 72h; |
71% | With lithium hydride | |
With lithium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 74h; | ||
With lithium hydride In N,N-dimethyl-formamide at 20℃; for 72h; | ||
Stage #1: malonic acid dimethyl ester With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydride In tetrahydrofuran for 2.25h; Inert atmosphere; Cooling with ice; Stage #2: Z-1,4-dichlorobutene In tetrahydrofuran at 40 - 45℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 7h; Inert atmosphere; | |
93% | In dichloromethane for 72h; Heating; | |
93.2% | In dichloromethane at 20℃; for 0.25h; |
88% | With Grubbs catalyst first generation In dichloromethane at 20℃; for 20h; | |
82% | In methanol; water at 50℃; for 1.5h; | |
82% | With Grubbs catalyst first generation In dichloromethane at 20℃; for 1h; Inert atmosphere; | |
80% | In dichloromethane at 20℃; for 8h; | |
77% | With RuH2Cl2(P(t-Bu)2Me)2; phenylacetylene In dichloromethane at 20℃; for 4.5h; Schlenk technique; Sealed tube; Inert atmosphere; | General Method for 1,3-Diene Synthesis General procedure: To an oven-dried 50 mL Schlenk tube with magnetic stir bar was added in an argon(g)-filled glovebox, RuH2Cl2(P(t-Bu)2Me)2 (4.9 mg, 0.010 mmol; 5 mol %), 2 mL of dichloromethane, and enyne (0.20 mmol) dissolved in 2 mL of dichloromethane (4 mL). The sealed tube was then removed from the glovebox and placed under a positive stream of argon(g) and the solution stirred for 24 hours. The reaction mixture was then filtered through a pipette plugged with ca. 3.0 cm of celite, and the Schlenk tube was rinsed with either Et2O (tetrahydropyran and dihydrofuransubstrates) or EtOAc (2 x 2 mL) and washed through the celite plug. The solution was concentrated down and there sulting yield was determined by 1H NMR based on the terminal diene signal as compared to the internal mesitylene standard. The solutions were then purified by flash column chromatography with silica gel using the listed solvent systems. |
92 % Chromat. | In dichloromethane at 80℃; for 0.05h; MW irradiation; | |
99 % Chromat. | In dichloromethane at 25℃; for 20h; | |
With Grubbs catalyst first generation | ||
95 %Spectr. | With C45H67Cl2O4PRu In dichloromethane-d2 at 40℃; for 11h; Inert atmosphere; | |
> 99 %Chromat. | With 1,4-bis[4-Oipr-5-(4,5-dihydroIMES)Cl2Ru=CH]pyrimidin-2-ylpiperazine In dichloromethane at 25℃; for 2h; Inert atmosphere; | |
With [3-(2,6-diisopropylphenyl)-1,3-diaza[3.3.1]non-2-ylidene]dichloro(2-isopropoxyphenylmethylene)-ruthenium In benzene-d6 at 25℃; for 2h; Inert atmosphere; Schlenk technique; | ||
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 65℃; for 4h; Inert atmosphere; | ||
With C43H50Cl2N2ORu In chloroform-d1 at 30℃; | ||
With C36H44Cl2N2O2Ru In (2)H8-toluene at 70℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: formaldehyd; Dimethyl 3-cyclopentene-1,1-dicarboxylate With sulfuric acid; acetic acid at 60℃; for 24h; Stage #2: With chloro-trimethyl-silane In methanol for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: malonic acid dimethyl ester With sodium methylate In methanol at 0 - 20℃; for 0.666667h; Stage #2: 1,4-dichloro-2-butene In methanol at 0 - 20℃; for 12h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chloride; dimethyl sulfoxide; In water; | Method A A well stirred mixture of 9.2 g (0.05 mol) of dimethyl 3-cyclopentene-1,1-dicarboxylate, 3.6 g (0.06 mol) of sodium chloride, 1.8 ml (0.1 mol) of water and 30 ml of dimethyl sulfoxide was heated, under nitrogen, in an oil bath to 160-165C and kept at this temperature for 18 hours. The progress of the reaction could be conveniently monitored by gas chromatographic analysis. The dark mixture was then cooled to room temperature, poured onto 200 ml of saturated sodium chloride solution and extracted with ether (3 x 100 ml). The combined extracts were washed with saturated aqueous sodium chloride (50 ml), dried over magnesium sulfate and evaporated, leaving 5.1 g (79%) of crude methyl 3-cyclopentene-1-carboxylate. Distillation gave 4.2 g (70%) of pure material, b.p. 147-148C, as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid at 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C | ||
Multi-step reaction with 12 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C | ||
Multi-step reaction with 10 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 54 percent / TMSBr / acetonitrile / 16 h / 20 °C | ||
Multi-step reaction with 14 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 54 percent / TMSBr / acetonitrile / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 100 percent / H2 / Pd/C / ethanol / 18 h / 20 °C / 760 Torr 17.1: 20 percent / TMSBr / acetonitrile / 16 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 100 percent / H2 / Pd/C / ethanol / 18 h / 20 °C / 760 Torr 15.1: 20 percent / TMSBr / acetonitrile / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 15 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C | ||
Multi-step reaction with 13 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating | ||
Multi-step reaction with 5 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 100 percent / H2 / Pd/C / ethanol / 18 h / 20 °C / 760 Torr | ||
Multi-step reaction with 14 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 100 percent / H2 / Pd/C / ethanol / 18 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C | ||
Multi-step reaction with 6 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 17.1: 29 percent / TMSBr / acetonitrile / 16 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 15.1: 29 percent / TMSBr / acetonitrile / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 17.1: 12 percent / TMSBr / acetonitrile / 16 h / 20 °C | ||
Multi-step reaction with 17 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 29 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 17.1: 59 percent / TMSBr / acetonitrile / 48 h / 20 °C | ||
Multi-step reaction with 15 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 15.1: 12 percent / TMSBr / acetonitrile / 16 h / 20 °C |
Multi-step reaction with 15 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 29 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C 15.1: 59 percent / TMSBr / acetonitrile / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h | ||
Multi-step reaction with 7 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C | ||
Multi-step reaction with 14 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 12 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating 14.1: butan-2-one / 65 h / 120 °C 15.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 16.1: 29 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C | ||
Multi-step reaction with 14 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating 12.1: butan-2-one / 65 h / 120 °C 13.1: 47 percent / LiH / Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 50 °C 14.1: 29 percent / aq. OsO4; NMO / acetone / 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5: TBAF / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C | ||
Multi-step reaction with 8 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5: TBAF / tetrahydrofuran / 1 h / 20 °C 6: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C | ||
Multi-step reaction with 4 steps 1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C | ||
Multi-step reaction with 9 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C 4.1: 97 percent / MCPBA / CH2Cl2 / 1 h / 0 - 20 °C 5.1: TBAF / tetrahydrofuran / 1 h / 20 °C 6.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 7.1: NaBH4 / ethanol / 0 °C 7.2: ethanol / 1 h / Heating 8.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 9.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 10.1: 10 g / butan-1-ol / 0.67 h / 50 °C 11.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 12.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 13.1: NaI / butan-2-one / 5 h / Heating | ||
Multi-step reaction with 11 steps 1.1: 78 percent / LiCl / dimethylsulfoxide / 3 h / 150 °C 2.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 89 percent / TBHP / VO(acac)2 / CH2Cl2 / 48 h / 20 °C 4.1: 100 percent / imidazole / CH2Cl2 / 2 h / 20 °C 5.1: NaBH4 / ethanol / 0 °C 5.2: ethanol / 1 h / Heating 6.1: Et3N; DMAP / CH2Cl2 / 16 h / 0 - 20 °C 7.1: aq. H2O2; i-Pr2NEt / CH2Cl2 / 0.25 h 8.1: 10 g / butan-1-ol / 0.67 h / 50 °C 9.1: 40 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 10.1: 98 percent / Et3N; DMAP / 48 h / 0 °C 11.1: NaI / butan-2-one / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / NaOMe / methanol / 3 h / 0 - 20 °C 2: 93 percent / Grubbs' catalyst / CH2Cl2 / 72 h / Heating | ||
Multi-step reaction with 2 steps 1: sodium hydride; tetrakis(triphenylphosphine) palladium(0) / 1,2-dichloro-ethane / 24 h / 65 °C / Inert atmosphere 2: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 65 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: CH3COOH; H2SO4 / 24 h / 60 °C 1.2: 60 percent / trimethylsilyl chloride / methanol / 3 h / Heating 2.1: 25 percent / porcine pancreatin / various solvent(s) / 3.5 h / 25 °C 3.1: 90 percent / imidazole / dimethylformamide / 10 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: H2SO4; AcOH / 24 h / 60 °C 1.2: TMSCl / methanol 1.3: 25 percent / pancreatin 2.1: imidazole | ||
Multi-step reaction with 2 steps 1.1: AcOH; H2SO4 1.2: TMSCl / methanol / Enzymatic reaction 2.1: 90 percent / imidazole |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: H2SO4; AcOH / 24 h / 60 °C 1.2: TMSCl / methanol 1.3: 25 percent / pancreatin 2.1: imidazole 3.1: 68 percent / tBuOK / dimethylsulfoxide / 0.25 h / 20 °C 4.1: 99 percent / TMSCl / methanol / 0.25 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: AcOH; H2SO4 1.2: TMSCl / methanol / Enzymatic reaction 2.1: 90 percent / imidazole 3.1: t-BuOK 3.2: 66 percent / TMSCl / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 82 percent / KOH / methanol / 20 h / 20 °C 2: 84 percent / SOCl2 / toluene / 2 h / Heating 3: NaN3 / acetone; H2O / 0.5 h / 0 °C 4: SnCl4 / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: water; potassium hydroxide / tetrahydrofuran / 1 h / 0 °C 2: sodium azide; tetrabutylammomium bromide; zinc trifluoromethanesulfonate / tetrahydrofuran / 48 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With water; potassium hydroxide In ethanol at 45℃; for 14h; Inert atmosphere; Stage #2: at 180℃; for 1h; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: 45percent KOH / aq. ethanol / 15 h / Heating 2: 100 percent / 1 h / 185 - 195 °C | ||
Multi-step reaction with 2 steps 1: water; potassium hydroxide / ethanol / 1 h / Reflux 2: 1 h / 180 °C / Neat (no solvent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | 13 (Dimethyl 3-Cyclopentene-1,1-dicarboxylate) To a flame dried round-bottomed flask was placed dimethyl malonate (ACROS, 99+%, 26.7 g, 23.1 mL, 200 mmol) and anhydrous dimethylformamide (DMF, 300 mL). The mixture was cooled to 0° C. under an atmosphere of nitrogen while stirring. To this solution was then added lithium hydride (ACROS, 98%, 4.06 g,500 mmol) powder in one portion. The resulting mixture was allowed to stir at 0° C. until the evolution of hydrogen ceased (~3 hours). To this heterogeneous mixture was then slowly added cis-1,4-dichloro-2-butene (ACROS, 95%, 30 g, 25.3 mL, 228 mmol). The resulting mixture was allowed to slowly come to room temperature and then allowed to stir for 72 hours (the color of the heterogeneous mixture changed from white to brown overnight). The reaction progress was monitored by TLC (silica gel, 20% ethyl ether/hexanes). The reaction mixture was diluted with 20% ethyl ether/hexanes (500 mL) and the solution poured into cold water (350 mL). The organic phase was separated, washed successively with water (300 mL) and brine (300 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a light yellow solid. The crude material was recrystallized from refluxing hexanes (or ethyl ether). The desired dimethyl diester 2 was obtained as white needles in 50% yield. Mp (DSC) 63.48° C., 1H-NMR (CD13, 300 MHz) δ5.56 (s, 2H), 3.68 (2s, 6H), 2.97 (s, 4H); 13C-NMR (CDCl3, 300 MHz) δ172.47, 127.64, 58.60, 52.66, 40.78; FT-IR (CH2Cl2) (cm-1) 3061, 2955, 1733, 1624, 1436, 1266, 1076, 975. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | 14 (Dimethyl 3-Cyclopentene-1,1-dicarboxylate) To a flame dried round-bottomed flask was placed dimethyl malonate (ACROS, 99+%, 26.7 g, 23.1 mL, 200 mmol) and anhydrous dimethylformamid (DMF, 300 mL). The mixture was cooled to 0° C. under an atmosphere of nitrogen while stirring. To this solution was then added lithium hydride (ACROS, 98%, 4.06 g, 500 mmol) powder in one portion. The resulting mixture was allowed to stir at 0° C. until the evolution of hydrogen ceased (~3 hours). To this heterogeneous mixture was then slowly added cis-1,4-dichloro-2-butene (ACROS, 95%, 30 g, 25.3 mL, 228 mmol). The resulting mixture was allowed to slowly come to room temperature and then allowed to stir for 72 hours (the color of the heterogeneous mixture changed from white to brown overnight). The reaction progress was monitored by TLC (silica gel, 20% ethyl ether/hexanes). The reaction mixture was diluted with 20% ethyl ether/hexanes (500 mL) and the solution poured into cold water (350 mL). The organic phase was separated, washed successively with water (300 mL) and brine (300 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a light yellow solid. The crude material was recrystallized from refluxing hexanes (or ethyl ether). The desired dimethyl diester 1 was obtained as white needles in 50% yield. Mp (DSC) 63.48° C.; 1H-NMR (CDCl3, 300 MHz) δ5.56 (s, 2H), 3.68 (2s, 6H), 2.97 (s, 4H); 13C-NMR (CDCl3, 300 Mhz) δ172.47, 127.64, 58.60, 52.66, 40.78; FT-IR (CH2Cl2) (cm-1) 3061, 2955, 1733, 1624, 1436, 1266, 1076, 975. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; potassium hydroxide; In methanol; water; | Method B A solution of 26.0 g (0.39 mol as 100%) of 85% potassium hydroxide pellets in 280 ml of methanol was added dropwise with stirring, under nitrogen, to a solution of 76.8 g (0.41 mol) of dimethyl 3-cyclopentene-1,1-dicarboxylate in 280 ml of methanol during 1 hour. The resulting mixture was stirred for an additional 2 hours at room temperature after which the methanol was removed at reduced pressure. The solid residue was dissolved in 125 ml of water and this solution was cooled to 0-5C and acidified by the dropwise addition of 82 ml of 5N hydrochloric acid, added over 30 minutes while maintaining the reaction temperature below 10C. The mixture was then extracted with ether (3 x 300 ml) and dried over magnesium sulfate. Evaporation of the ether left 64.0 g (92%) of methyl 3-cyclopentene-1-carboxy-1-carboxylate as a sticky, white powder. The isolated methyl 3-cyclopentene-1-carboxy-1-carboxylate was charged to a 3-necked, 100 ml round-bottomed flask set for downward distillation. Powdered glass (12.0 g) was then added and this mixture heated to 155-160C in an oil bath under a sweep of dry nitrogen and with good stirring at which point decarboxylation commenced. Clean methyl 3-cyclopentene-1-carboxylate distills as it is produced, b.p. 147-148C. The pot temperature was slowly raised to 180C to ensure that all of the produced methyl 3-cyclopentene-1-carboxylate distilled. In this manner, 40.2 g (78% for the 2 steps) of pure methyl 3-cyclopentene-1-carboxylate as a colorless oil, was collected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Inert atmosphere; Stage #2: With sodium hydroxide; water In diethyl ether | |
85% | With lithium aluminium tetrahydride In diethyl ether at 20℃; for 16h; | |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: dimethyl allylmalonate With sodium hydride In dichloromethane Stage #2: Allyl acetate In dichloromethane for 1h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: Allyl acetate; malonic acid dimethyl ester With sodium hydride In dichloromethane at 20℃; Stage #2: In dichloromethane for 4h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 22% 2: 8% | With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 2: dicobalt octacarbonyl; tetraphenylporphyrinchromium(III) chloride / tetrahydrofuran / 16 h / 70 °C / 25858.1 Torr / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With lithium hydride In N,N-dimethyl-formamide at 20℃; for 64h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium diacetate In carbonic acid dimethyl ester at 25℃; for 18h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. | |
82 % ee | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With (R)-3,3'-bis[2,4,6-tricyclohexylphenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; potassium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: 4-methoxybenzenediazonium tetrafluoroborate With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether; benzene at 10℃; for 24h; Overall yield = 73 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. | |
85 % ee | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With (R)-3,3'-bis[2,4,6-tricyclohexylphenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; potassium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: 4-biphenyldiazonium tetrafluoroborate With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether; benzene at 10℃; for 24h; Overall yield = 66 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. | |
84 % ee | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With (R)-3,3'-bis[2,4,6-tricyclohexylphenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; potassium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: 3-(trifluoromethyl)benzenediazonium tetrafluoroborate With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether; benzene at 10℃; for 24h; Overall yield = 70 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With palladium(II) trifluoroacetate; zinc trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine In methanol at 60℃; for 2.66667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-di-tert-butyl-4-methylpyridine; palladium(II) trifluoroacetate; (S,S)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole In methanol at 60℃; for 1h; enantioselective reaction; | General experimental procedure for the enantioselective Heck-Matsuda reaction General procedure: A capped test tube (inside diameter 15 mm; length 85 mm), equipped with a magnetic stir bar was charged with Pd(CF3CO2)2 (4.5 mg, 0.0135 mmol), the ligand II (8.7 mg, 0.027 mmol) and methanol (1 mL). The solution was stirred at 60 °C for 5 minutes. After this time, DTBMP (27.7 mg, 0.135 mmol), the olefin (0.135 mmol) and the arenediazonium salt (0.27 mmol) were added sequentially. The reaction was left stirring until complete consumption of the starting material as indicated by TLC. Upon completion, the reaction mixture was loaded directly onto silica gel and chromatographed using hexanes/ethyl acetate (85/15) as eluent to give the desired Heck adducts. | |
80 % ee | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With (R)-3,3'-bis[2,4,6-tricyclohexylphenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; potassium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: (3-chloro-4-methoxyphenyl)diazonium tetrafluoroborate With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether; benzene at 10℃; for 24h; Overall yield = 80 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tert.-butylnitrite; methanesulfonic acid; palladium diacetate In methanol at 25℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With tert.-butylnitrite; methanesulfonic acid; palladium diacetate In methanol at 25℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 53 %Spectr. 2: 23 %Spectr. | With tetradeuterioacetic acid; C25H38O6PRu(1+)*BF4(1-); tris(1-methylethyl)phosphine at 90℃; for 168h; | |
1: 51 %Spectr. 2: 19 %Spectr. | With tetradeuterioacetic acid; C25H38O6PRu(1+)*BF4(1-) In dichloromethane at 60℃; for 68h; Overall yield = 60 %Spectr.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With N,N,N,N,-tetramethylethylenediamine; tetrabutylammonium tricarbonylnitrosylferrate In toluene at 80℃; for 72h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 18 h / -40 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 18 h / -40 - 20 °C / Inert atmosphere 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 18 h / -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 3.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 18 h / -40 - 20 °C / Inert atmosphere 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 4.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 4.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere 2.2: 18 h / -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 4.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 4.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide; water / ethanol / 14 h / 45 °C / Inert atmosphere 1.2: 255 / 1 h / 180 °C / Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2.2: -40 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; benzyl-(3,5-dioxa-4-phospha-cyclohepta[2,1-<i>a</i>;3,4-<i>a</i>']dinaphthalen-4-yl)-phenyl-amine; 4,4,6-trimethyl-1,3,2-dioxaborinane / tetrahydrofuran / 40 °C / Inert atmosphere 4.2: 2 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C34H36BrCl2N4ORu In toluene at 80℃; for 1.5h; Schlenk technique; Inert atmosphere; | |
93 %Chromat. | With dichloro-(1,3-dimesityl-4,5-bis(dimethylamino)imidazol-2-ylidene)-(benzylidene)-(tricyclohexylphosphine)ruthenium(II) In toluene at 60℃; for 1h; Glovebox; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With sodium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: benzenediazonium tetrafluoroborate With tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl methyl ether; benzene at 10℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | Stage #1: Dimethyl 3-cyclopentene-1,1-dicarboxylate With (R)-3,3'-bis[2,4,6-tricyclohexylphenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; potassium carbonate In tert-butyl methyl ether; benzene at 20℃; for 0.166667h; Stage #2: 2-fluorobenzenediazonium tetrafluoroborate In tert-butyl methyl ether; benzene at 10℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium carbonate; eosin y; triisopropylsilanethiol In 1,4-dioxane; water at 36 - 38℃; for 24h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C89H89Cl2N4ORu In n-heptane at 100℃; for 2.33333h; Inert atmosphere; | 24 Intramolecular cyclization metathesis of olefins:Weigh 1.0 g of dimethyl diallyl malonate,Add 2 mL of n-heptane,Stirring with nitrogen at room temperature for 20 minutes;Weigh different amounts of catalyst,Dissolved with 1 mL of n-heptane and added to the reactor,The temperature was raised to 100 ° C, the reaction was carried out for 120 minutes, and the conversion was calculated or tested. The results are shown in Table 1 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; chlorobis(cyclooctene)-iridium(I) dimer; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,4-dioxane at 120℃; |
Tags: 84646-68-4 synthesis path| 84646-68-4 SDS| 84646-68-4 COA| 84646-68-4 purity| 84646-68-4 application| 84646-68-4 NMR| 84646-68-4 COA| 84646-68-4 structure
[ 76910-08-2 ]
1-(Ethoxycarbonyl)-3-cyclopentene-1-carboxylic Acid
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[ 21622-00-4 ]
Diethyl 3-Cyclopentene-1,1-dicarboxylate
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[ 93981-13-6 ]
Diethyl 2-allyl-2-(cyclopent-2-en-1-yl)malonate
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[ 38511-09-0 ]
Diethyl cyclohex-3-ene-1,1-dicarboxylate
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[ 53608-93-8 ]
Diethyl 2-(cyclopent-2-en-1-yl)malonate
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[ 76910-08-2 ]
1-(Ethoxycarbonyl)-3-cyclopentene-1-carboxylic Acid
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[ 21622-00-4 ]
Diethyl 3-Cyclopentene-1,1-dicarboxylate
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[ 93981-13-6 ]
Diethyl 2-allyl-2-(cyclopent-2-en-1-yl)malonate
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[ 38511-09-0 ]
Diethyl cyclohex-3-ene-1,1-dicarboxylate
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[ 53608-93-8 ]
Diethyl 2-(cyclopent-2-en-1-yl)malonate
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[ 76910-08-2 ]
1-(Ethoxycarbonyl)-3-cyclopentene-1-carboxylic Acid
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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