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CAS No. : | 1617-18-1 | MDL No. : | MFCD07779251 |
Formula : | C6H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BFMKFCLXZSUVPI-UHFFFAOYSA-N |
M.W : | 114.14 | Pubchem ID : | 74172 |
Synonyms : |
|
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210 | UN#: | 3272 |
Hazard Statements: | H225 | Packing Group: | Ⅱ |
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 |
---|---|---|
With platinum on activated charcoal |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With sulfuric acid In water for 4h; Heating / reflux; | 8.13 Vinylacetic acid (10.0 g, 0.12 mol) was dissolved in ethanol (200 mL) and conc. sulfuric acid (0.75 mL, 0.014 mol) was added. The reaction was heated to reflux for 4 h. Crude reaction was diluted with ethyl acetate (200 mL), washed H2O (200 mL), sat. NaHCO3 (200 mL), dried MgSO4, and evaporated to dryness to afford 1 a clear oil (3.17 g, 23%). |
With hydrogenchloride | ||
With toluene-4-sulfonic acid |
In benzene Heating; | ||
In benzene Heating; | ||
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrachloromethane; chlorine at 10 - 20℃; Behandlung des Reaktionsprodukts mit Natriumaethylat-Loesung bei -5grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; <i>tert</i>-butyl alcohol at 15 - 25℃; folgendes Behandeln mit Natriumaethylat-Loesung bei 0grad; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether; sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetraethylammonium tosylate In N,N-dimethyl-formamide (electrolysis); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,2-dimethyl-1H-imidazole In diethyl ether for 144h; Irradiation; | |
In <i>tert</i>-butyl alcohol Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In toluene for 15h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With benzophenone In toluene for 168h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 65℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.7% | With 2,2'-azobis(isobutyronitrile) In n-heptane at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With n-Amyl nitrite In acetic acid at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With hydrazine hydrate In ethanol for 19h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | at 50℃; for 5h; | |
79% | at 50℃; for 5h; | |
67 % Chromat. | With palladium diacetate; triphenylphosphine at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With (trimethylstannyl)methyl-lithium at -78℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With lithium cyclohexylisopropylamide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 25℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 17% 2: 72% | In ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With magnesium In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 40% 2: 45 % Chromat. | With dicobalt octacarbonyl; tetra-(n-butyl)ammonium iodide In benzene at 25℃; for 6h; | |
1: 45 % Chromat. 2: 20% | With dicobalt octacarbonyl; tetra-(n-butyl)ammonium iodide In benzene at 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With magnesium In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 57% 2: 16% | With hydrogen at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 57% | With carbon monoxide; hydrogen at 120℃; for 4h; | |
1: 20% 2: 33% | at 120℃; for 4h; pressure vessel; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 27% 2: 55% | With hydrogen at 120℃; for 4h; | |
1: 27 % Turnov. 2: 55 % Turnov. | at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 55% 2: 27% | With carbon monoxide; hydrogen at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 7% 2: 33% | With hydrogen at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 33% 2: 7% | With carbon monoxide; hydrogen at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.1 % Chromat. | With palladium diacetate; potassium carbonate at 20℃; for 0.583333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 12 % Turnov. 2: 28% | at 120℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; | |
87% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 20℃; for 6h; Inert atmosphere; | |
70% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 6h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Stage #1: ethyl 3-butenoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -50 - -30℃; for 0.5h; Stage #2: 2,2-difluoropent-4-enenitrile In tetrahydrofuran; hexane at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Stage #1: triethylene glucol monomethyl ether; ethyl 3-butenoate With sodium In tetrahydrofuran for 4h; Stage #2: With hydrogenchloride In water | 8.14 Triethylene glycol monomethyl ether (4.27 g, 0.026 mol) and But-3-enoic acid ethyl ester (1.5 g, 0.013 mol) were dissolved in tetrahydrofuran (10 mL). Then lump Na0 (0.030 g, 0.013 mol) was added and the reaction was stirred for 4 h. Crude reaction was quenched with 1M HCl (20 mL), washed ethyl acetate (3×20 mL). Organic layers were combined and washed with H2O (2×10 mL), dried MgSO4, and evaporated to dryness to afford 2 a yellowish oil (1.07 g, 30% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; CuCl / tetrahydrofuran / 20 °C | ||
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / -78 °C | ||
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C | ||
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / (S)-tol-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; Cu(OTf)2 / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: n-BuLi; N,N'-diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C 2: tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / -78 °C | ||
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.08 h / 0 °C / Inert atmosphere 2: dichloromethane / 14.25 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2: 30 percent / (R,R)-salen-Co; AcOH / H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C 5.1: 98 percent / AgNO3; N-bromosuccinimide; H2O / acetone; hexane / 3 h / 20 °C 6.1: Bu3SnH / Pd(PPh3)4 / tetrahydrofuran / 2 h / -78 - 20 °C 6.2: I2 / tetrahydrofuran / 0.5 h / 0 °C 7.1: 52 percent / copper(I) thiophenecarboxylate; 1,10-phenanthroline; 1,5-diphenyl-1,4-pentadien-3-one / Cs2CO3 / N,N-dimethyl-acetamide / 17 h / 65 °C 8.1: 99 percent / TBAF / tetrahydrofuran / 0.67 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C 5.1: 98 percent / AgNO3; N-bromosuccinimide; H2O / acetone; hexane / 3 h / 20 °C 6.1: Bu3SnH / Pd(PPh3)4 / tetrahydrofuran / 2 h / -78 - 20 °C 6.2: I2 / tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C 5.1: 98 percent / AgNO3; N-bromosuccinimide; H2O / acetone; hexane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 100 percent / m-CPBA / CH2Cl2 / 20 °C 2.1: 30 percent / (R,R)-salen-Co; AcOH / H2O 3.1: n-BuLi / toluene / 0.25 h / -35 °C 3.2: Et2AlCl / toluene; hexane / 1 h / 0 °C 3.3: 72 percent / toluene / 2 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C 5.1: 98 percent / AgNO3; N-bromosuccinimide; H2O / acetone; hexane / 3 h / 20 °C 6.1: Bu3SnH / Pd(PPh3)4 / tetrahydrofuran / 2 h / -78 - 20 °C 6.2: I2 / tetrahydrofuran / 0.5 h / 0 °C 7.1: 52 percent / copper(I) thiophenecarboxylate; 1,10-phenanthroline; 1,5-diphenyl-1,4-pentadien-3-one / Cs2CO3 / N,N-dimethyl-acetamide / 17 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 5 h / 20 °C 2: PdCl2(dppf); K3PO4 / tetrahydrofuran / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 5 h / 20 °C 2: PdCl2(dppf); K3PO4 / tetrahydrofuran / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tributylphosphine; triethylamine In N,N-dimethyl-formamide at 100℃; | ||
With hydrogenchloride; tributylphosphine; triethylamine In N,N-dimethyl-formamide | 77 ethyl (2E)-3-[2-[4-(3,4-diethoxyphenyl)-4-oxobutanoyl]amino}-4-(4-methylphenyl)quinoline-6-yl]acrylate Example 77 ethyl (2E)-3-[2-[4-(3,4-diethoxyphenyl)-4-oxobutanoyl]amino}-4-(4-methylphenyl)quinoline-6-yl]acrylate N-[6-Bromo-4-(4-methylphenyl)quinolin-2-yl]-4-(3,4-diethoxyphenyl)-4-oxobutanamide obtained in Example 76 (560 mg), ethyl vinylacetate (0.22 mL), palladium acetate (11 mg), tributylphosphine (0.025 mL) and triethylamine (0.28 mL) were dissolved in DMF (5.6 mL), and the mixture was stirred overnight at 100°C. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography to give the title compound (350 mg). 1H-NMR(300 MHz, DMSO-d6) δppm 1.25 (3 H, t, J=7.2 Hz) 1.34 (6 H, q, J=6.8 Hz) 2.43 (3 H, s) 2.84 (2 H, t, J=5.9 Hz) 3.31 (2 H, t, J=5.9 Hz) 4.02 - 4.24 (6 H, m) 6.64 (1 H, d, J=16.0 Hz) 7.06 (1 H, d, J=8.5 Hz) 7.37 - 7.49 (5 H, m) 7.65 (1 H, dd, J=8.5, 1.9 Hz) 7.73 (1 H, d, J=16.0 Hz) 7.87 (1 H, d, J=8.8 Hz) 7.96 (1 H, d, J=1.3 Hz) 8.16 (1 H, dd, J=8.8, 1.7 Hz) 8.26 (1 H, s) 11.09 (1 H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; tetrabutylammomium bromide In toluene | 6.a EXAMPLE 6 (a) Ethyl 2,3-dihydro-2-vinyl-1H-indene-2-carboxylate. Tetrabutylammonium bromide (0.31 g) and 48% NaOH solution (9 ml) were added to a flask. α,α'-dibromo-o-xylene (5.0 g) in toluene (15 ml) was then added to the flask. The mixture was stirred and ethyl 3-butenoate (2.16 g) in toluene (15 ml) was added dropwise at room temperature. After the addition the temperature was slowly raised to +60° C. The mixture was stirred at this temperature for 3.5 hours and then cooled. The toluene layer was separated, washed with water and evaporated at reduced pressure to give the desired product. Mass spectrogram: 216 (17, M+.), 143 (100), 142 (62), 141 (42), 128 (50), 115 (38) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; tetrabutylammomium bromide In toluene | 6.a a) a) Ethyl 2,3-dihydro-2-vinyl-1H-indene-2-carboxylate. Tetrabutylammonium bromide (0.31 g) and 48% NaOH solution (9 ml) were added to a flask. α,α--dibromo-o-xylene (5.0 g) in toluene (15 ml) was then added to the flask. The mixture was stirred and ethyl 3-butenoate (2.16 g) in toluene (15 ml) was added dropwise at room temperature. After the addition the temperature was slowly raised to +60°C. The mixture was stirred at this temperature for 3.5 hours and then cooled. The toluene layer was separated, washed with water and evaporated at reduced pressure to give the desired product. Mass spectrogram: 216 (17, M+.), 143 (100), 142 (62), 141 (42), 128 (50), 115 (38) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; N,N-dimethyl-formamide | XVII 3-(3-ethoxycarbonylpropyl)-benzaldehyde EXAMPLE XVII 3-(3-ethoxycarbonylpropyl)-benzaldehyde 6.3 g (55 mmol) ethyl vinylacetate are dissolved in 30 ml THF under a protective gas atmosphere. While cooling with ice 240 ml (120 mmol) of a 0.5 M solution of 9-BBN in THF are added dropwise. Then the reaction solution is left to warm up to ambient temperature and stirred for 1.5 hours. 100 ml DMF are added and 40 ml (120 mmol) of a 3 M aqueous K3PO4 solution are added dropwise. Then 6.6 ml (55 mmol) 3-bromobenzaldehyde and 2.2 g (3 mmol) [1,1 '-bis-(diphenylphosphino)-ferrocene]-palladium(II)-dichloride are added. The mixture is stirred for 16 hours at ambient temperature. Then the solvent is eliminated in vacuo. The residue is chromatographed on silica gel (petroleum ether/ethyl acetate=100:0→65:35). Yield: 5.7 g (47% of theory) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pentafluorosulfanyl chloride; triethyl borane In hexane at -30℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; acetic acid; p-benzoquinone In tetrahydrofuran at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; acetic acid; p-benzoquinone In 1,4-dioxane at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With barium isopropoxide; (S)-[1,1']-binaphthalenyl-2,2'-diol In 1,2-dimethoxyethane at 0℃; for 24h; Inert atmosphere; optical yield given as %ee; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: ethyl 3-butenoate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; for 1.5h; Stage #2: With potassium phosphate In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water Stage #3: m-bromobenzoic aldehyde In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 30% 2: 30% | Stage #1: ethyl 3-butenoate With lithium diisopropyl amide In tetrahydrofuran at -50℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-difluoropent-4-enenitrile In tetrahydrofuran at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: ethyl 3-butenoate With lithium diisopropyl amide In tetrahydrofuran at -50℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-difluoropent-4-enenitrile In tetrahydrofuran at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: ethyl 3-butenoate With lithium diisopropyl amide In tetrahydrofuran at -50℃; for 0.5h; Inert atmosphere; Stage #2: α,α-difluorobenzeneacetonitrile In tetrahydrofuran at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: ethyl 3-butenoate With lithium diisopropyl amide In tetrahydrofuran at -50℃; for 0.5h; Inert atmosphere; Stage #2: α,α-difluorobenzeneacetonitrile In tetrahydrofuran at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydride In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0℃; for 2.08333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In pentane at 0 - 20℃; for 3.33333h; Inert atmosphere; | |
85% | With triethylamine In toluene; phenol at 55℃; | 6.1; 6.2; 6.3 Example 6 step one:At room temperature,To a three-necked flask was added 600 parts of toluene,150 parts of triethylamine, 110 parts of ethanol,100 parts of crotonyl chloride were charged in a constant pressure separatory funnel,Under electric stirring, toluene,The mixture of triethylamine and ethanol is mixed well,While heating the mixture to 55 ° C,Then through the constant pressure funnel control crotonyl chloride uniform dropping 1h,Reaction overnight, gas chromatography to detect the progress of the reaction,Record the reaction time;Step two:The reaction is over,The reaction solution was cooled,The liquid is washed twice with water,Dried over anhydrous magnesium sulfate,Filtering, removing toluene solvent by rotary evaporation,3-butenoic acid hexyl ester to give a crude product;Step three:The crude 3-butenyl caproate obtained in step two is in a ratio by weight of crude product: silica gel = 3-4: 1With 120 mesh silica gel dry packing method,Then the volume ratio of petroleum ether - ethyl acetate gradient elution,The eluate obtained by eluting with petroleum ether-ethyl acetate in a volume ratio of 200: 1 was recovered,Rotary evaporation of petroleum ether - ethyl acetate,The product, hexyl 3-butenoate,Weight and calculate yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In (2)H8-toluene at 0℃; for 0.166667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran-d8 at 0℃; for 0.166667h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Inert atmosphere; | |
87% | With iron(III) sulfate hydrate; palladium dichloride In water; acetonitrile at 45℃; for 2.5h; Inert atmosphere; | |
85% | With chromium(VI) oxide; palladium dichloride In water; acetonitrile at 20 - 60℃; for 7h; | 4.2 General procedure for oxidation of terminal olefins General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5mol%) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60°C and stirred for specified time (see Tables 5-7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones. |
58% | With manganese(IV) oxide; palladium dichloride In water; acetonitrile at 60℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With aluminum (III) chloride; zinc In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In methanol at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 8% 2: 74% | With hydrazine hydrate In methanol; water at 20℃; for 5h; Cooling with ice; | 3.2.3. General Procedure for the Synthesis of Acyl Hydrazides 3a-3k General procedure: To a stirred solution of esters 2a-2j (70 mmol) in MeOH (30 mL) cooled in an ice-water bath was added dropwise 80% aqueous hydrazine hydrate (6.26 g, 100 mmol). The resulting solution was stirred at room temperature (2a-2b or 2d-2j), or reflux (2c), until the completion of reaction as indicated by TLC analysis (typically within 5 h). The reaction mixture was evaporated on a rotary evaporator to give a residue, which was purified by column chromatography through a short silica gel column to yield 3a-3k after trituration with n-hexane if possible. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: ethyl 3-butenoate; 2-bromo-6-iodo-1,4,5,8-tetramethoxynaphthalene With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 20℃; for 2h; Inert atmosphere; Reflux; Stage #2: With potassium osmate(VI) dihydrate; sodium hydrogencarbonate; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol at 20℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: ethyl 3-butenoate; 2-bromo-6-iodo-1,4,5,8-tetramethoxynaphthalene With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine at 20℃; for 2h; Inert atmosphere; Reflux; Stage #2: With potassium osmate(VI) dihydrate; sodium hydrogencarbonate; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol at 20℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Dimethylphenylsilane; water In dimethyl sulfoxide at 70℃; for 0.333333h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With dihydrogen hexachloroplatinate In tetrahydrofuran; benzene at -196 - 20℃; for 24h; Inert atmosphere; | 4.7. Synthesis of (n-Oct)Me3Si via successive hydrogenolysis andhydrosilylation using H2PtCl6 as a catalyst General procedure: Successive halogen exchange and hydrogenolysis of Me3SiCl(63 mL, 500 μmol) was similarly performed following the abovementioned procedure for the entry 1 in Table 2. To the resultingsolution containing Me3SiH, was added a THF solution of H2PtCl6(0.1M, 250 μL, 25 μmol) and 1-octene (72 μL, 500 μmol) at -196 °C.The mixture was stirred at room temperature for 24 h to give (n-Oct)Me3Si [420 μmol, 86% yield by 1H NMR analysis using cyclohexane(47 μL, 500 μmol) as an internal standard]. The reactionmixture was diluted with hexane (15 mL), filtered through a silicagelpad, and evaporated. The resulting colorless oil was purified byflash silica-gel column chromatography (eluent: hexane) to give (n-Oct)Me3Si (78 mg, 390 μmol, 78%) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide In diethyl ether at 35℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With oxygen; palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane; water In toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91 %Spectr. | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; [CoCl2(dmgH)2(pyridine)]; potassium carbonate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere; Sealed tube; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 % ee | With 2,6-dimethyl-4-chlorophenol; (1S,2S,4S)-1-(anthracen-9-ylmethyl)-2-((R)-((6-chloro-2,5-diphenylpyrimidin-4-yl)oxy)(6-isopropoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide; potassium hydroxide In ethanol; water; toluene at -40℃; for 20h; Overall yield = 63 percent; enantioselective reaction; |
Tags: 1617-18-1 synthesis path| 1617-18-1 SDS| 1617-18-1 COA| 1617-18-1 purity| 1617-18-1 application| 1617-18-1 NMR| 1617-18-1 COA| 1617-18-1 structure
[ 61444-38-0 ]
(Z)-(Z)-Hex-3-en-1-yl hex-3-enoate
Similarity: 0.92
[ 61444-37-9 ]
(E)-(E)-Hex-3-en-1-yl hex-3-enoate
Similarity: 0.92
[ 61444-38-0 ]
(Z)-(Z)-Hex-3-en-1-yl hex-3-enoate
Similarity: 0.92
[ 61444-38-0 ]
(Z)-(Z)-Hex-3-en-1-yl hex-3-enoate
Similarity: 0.92
[ 61444-37-9 ]
(E)-(E)-Hex-3-en-1-yl hex-3-enoate
Similarity: 0.92
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