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CAS No. : | 40231-03-6 | MDL No. : | MFCD03427125 |
Formula : | C9H12SSi | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OQUBLKNISPLGJP-UHFFFAOYSA-N |
M.W : | 180.34 | Pubchem ID : | 596870 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P403+P235 | UN#: | 1993 |
Hazard Statements: | H225 | Packing Group: | Ⅲ |
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 |
---|---|---|
92% | With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; for 6 h; Sealed tube | 2-[(trimethylsilyl)ethynyl]thiophene (1 mmol), inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) (0.05 mmol), 2 mL of DMA or DMSO solvent was sequentially added to a 10 mL sealed tube and heated and stirred in a 60° C. oil bath for 6 hours. The progress of the reaction was followed by TLC. The reaction was completed and an equivalent of mesitylene or n-undecane was added to the crude product. The exact yield of the product was determined by GC and GC-MS. According to GC and GC-MS, when DMSO is used as a reaction solvent, inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) is used as a catalyst, and the yields of the products are as follows: 59percent, 66percent, 75percent, 77percent, 92percent, 85percent. When DMA was used as the reaction solvent, the inorganic potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) was used as a catalyst, and the yield of the product was: 51percent, 60percent, respectively. 67percent, 70percent, 81percent, 72percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine; In tetrahydrofuran; at 80℃; | mixture of 2-iodothiophene (2.20 g, 10.5 mmol), trimethylsilylacetylene (2.0 mL, 14.5 mmol), PdCl2(PPh3)2 (65 mg, 0.093 mmol), CuI (14 mg, 0.074 mmol), and NEt3 (4 mL) in THF (16 mL) was stirred at 80 C. After stirring for 30 min, to the mixture was added aqueous 2 M HCl, and extracted with EtOAc (3 times). The organic phase was sequentially washed with brine, aqueous sat.NaHCO3, and brine, and dried with MgSO4. After concentration, the residue was purified by distillation to afford 2-(trimethylsilylethynyl)thiophene as colorless oil (1.57 g, 83%). colorless oil; Rf: 0.60 (hexane); 1H NMR (CDCl3, 400 MHz): 0.25 (s, 9H), 6.95 (dd, 1H, J = 4.4, 4.4 Hz), 7.23 (d, 1H, J = 4.4 Hz), 7.23 (d, 1H, J = 4.4 Hz); 13C NMR (CDCl3, 100 MHz): -0.2, 97.5, 98.7, 123.2, 126.8, 127.2, 132.6; IR (NaCl): vmax 3735, 3107, 3078, 2960, 2898, 2146, 2067, 1949, 1891, 1846, 1799, 1514, 1420, 1351, 1250, 1164, 1140, 1076, 1042, 844 cm-1; HRMS (DART): M+ calcd for C9H12SSi, 180.04290; found, 180.03286 |
70.02% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In tetrahydrofuran; at 20℃; for 16h;Inert atmosphere; | A mixture of 2-iodothiophene (500 mg, 2.38 mmol), Pd(PPh3)2Cl2 (52.95 mg, 0.0754 mmol), CuI (28.1 mg, 0.14756 mmol) and diisopropylamine (0.62 ml, 4.4744 mmol) in THF (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.453 ml, 3.284 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield 300 mg of trimethyl(thiophen-2-ylethynyl)silane (300 mg, 1.66 mol, yield 70.02%). |
With 5% palladium-copper on carbon; diethylamine; triphenylphosphine; In methanol; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation; | General procedure: In a microwave reaction vessel, the iodide derivative (0.5mmol, 1.0 eq), PPh3 (5mol%), diethylamine (1.5mmol) and Pd-Cu/C catalyst (5mol% Pd) were suspended in MeOH (3mL). The tube was sealed with a Teflon cap, the reaction mixture was flushed under an argon flow for 5minand then TMSA (1mmol) was added. Then, the reaction mixture was stirred 120C under microwave irradiations for 20min. After completion of the reaction, the azide derivative (0.6mmol) was added and the mixture was irradiated again for 10minat 120C. The mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) chloride; In dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere; | General procedure: A mixture of a (hetero)aryl iodide 3 (2.00 mmol), PdCl2(PPh3)2 (28.1 mg, 0.04 mmol,2 mol %), and CuCl (7.92 mg, 0.08 mmol, 4 mol %) was dissolved in DMSO (2.00mL) in a 80 mL microwave vessel equipped with a stirring bar and a septum and was degassed with N2 for 5 min. After addition of trimethylsilylacetylene (0.42 mL,3.00 mmol) and dry triethylamine (0.55 mL, 4.00 mmol) the solution was stirred atroom temperature for 1 h. | |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) chloride; In dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere; | General procedure: A mixture of a (hetero)aryl iodide 1 (2.00 mmol), Pd(PPh3)2Cl2(28.1 mg, 0.04 mmol, 2 mol%), and CuCl (7.92 mg, 0.08 mmol, 4mol%) was dissolved in DMSO (1.00 mL) in a 8 mL microwavevessel equipped with a stirring bar and a septum and was degassedwith N2 for 5 min. After the addition of TMSA (0.42 mL,3.00 mmol) and anhydrous Et3N (0.55 mL, 4.00 mmol), the solutionwas stirred at r.t. for 1 h. Then, KF (232 mg, 4.00 mmol) wasadded and the reaction mixture was vigorously stirred under air inthe open reaction vessel at r.t. for 16 h. After the addition of themethanethiol 2 (or 6, 8) (1.20 mmol, 0.6 equiv), KOH (224 mg,4 mmol), and DMSO (1.00 mL), the mixture was heated in the microwavecavity at 130C for 1 h. After cooling to r.t., the solventswere removed under reduced pressure. The residue was absorbed onCelite and purified by column chromatography on silica gel with n-hexane or n-hexane-THF (100:1) as eluent. The experimental detailsare shown in Table 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium trimethylsilonate; In dimethyl sulfoxide; at 60℃; under 760.051 Torr; for 6h;Sealed tube;Catalytic behavior; | 2-[(trimethylsilyl)ethynyl]thiophene (1 mmol), inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) (0.05 mmol), 2 mL of DMA or DMSO solvent was sequentially added to a 10 mL sealed tube and heated and stirred in a 60 C. oil bath for 6 hours. The progress of the reaction was followed by TLC. The reaction was completed and an equivalent of mesitylene or n-undecane was added to the crude product. The exact yield of the product was determined by GC and GC-MS. According to GC and GC-MS, when DMSO is used as a reaction solvent, inorganic base potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) is used as a catalyst, and the yields of the products are as follows: 59%, 66%, 75%, 77%, 92%, 85%. When DMA was used as the reaction solvent, the inorganic potassium tert-butoxide (sodium) or potassium hydroxide (sodium) or potassium trimethylsilylate (sodium) was used as a catalyst, and the yield of the product was: 51%, 60%, respectively. 67%, 70%, 81%, 72%. |
With tetra-n-butylammoniumfluoride trihydrate; In tetrahydrofuran; water; | Step C 2-Ethynylthiophene Under a nitrogen atmosphere a solution of 3.3 grams (0.018 mole) of 2-trimethylsilylethynylthiophene in 50 ml of tetrahydrofuran was stirred, and 5.8 grams (0.018 mole) of tetrabutylammonium fluoride trihydrate was added. Upon completion of addition, the reaction mixture was stirred for 30 minutes. After this time the reaction mixture was taken up in 100 ml of water and was extracted with three 75 ml portions of diethyl ether. The combined extracts were washed with three portions of water and with one portion of an aqueous solution saturated with sodium chloride. The organic layer was filtered through silica gel, and the filtrate was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated, yielding 2.0 grams of 2-ethynylthiophene. Steps A-C were repeated several times. | |
With potassium fluoride; at 20℃; for 16h; | General procedure: A mixture of a (hetero)aryl iodide 1 (2.00 mmol), Pd(PPh3)2Cl2(28.1 mg, 0.04 mmol, 2 mol%), and CuCl (7.92 mg, 0.08 mmol, 4mol%) was dissolved in DMSO (1.00 mL) in a 8 mL microwavevessel equipped with a stirring bar and a septum and was degassedwith N2 for 5 min. After the addition of TMSA (0.42 mL,3.00 mmol) and anhydrous Et3N (0.55 mL, 4.00 mmol), the solutionwas stirred at r.t. for 1 h. Then, KF (232 mg, 4.00 mmol) wasadded and the reaction mixture was vigorously stirred under air inthe open reaction vessel at r.t. for 16 h. After the addition of themethanethiol 2 (or 6, 8) (1.20 mmol, 0.6 equiv), KOH (224 mg,4 mmol), and DMSO (1.00 mL), the mixture was heated in the microwavecavity at 130C for 1 h. After cooling to r.t., the solventswere removed under reduced pressure. The residue was absorbed onCelite and purified by column chromatography on silica gel with n-hexane or n-hexane-THF (100:1) as eluent. The experimental detailsare shown in Table 2. |
350 mg | With methanol; potassium carbonate; at 20℃; for 1h; | To a solution of <strong>[40231-03-6]trimethyl(thiophen-2-ylethynyl)silane</strong> (560 mg, 3.11 mmol) in methanol (6 mL) was added potassium carbonate (858 mg, 6.21 mmol) and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a colorless oil (350 mg). To a solution of the obtained colorless oil (350 mg) in acetonitrile (3 mL) were added 3-azidopiperidine-2,6-dione (synthesized by the method of Example 1 (1-1)) (479 mg, 3.11 mmol) and copper(I) iodide (59.1 mg, 0.31 mmol) and the mixture was stirred at room temperature for 20 hr. The precipitate was collected by filtration and washed with methanol to give 3-[4-(thiophen-2-yl)-1H-1,2,3-triazol-1-yl]piperidine-2,6-dione (429 mg, 53%) as a gray solid. 1H-NMR(DMSO-d6) δ 11.28(1H, brs), 8.60(1H, s), 7.56(1H, dd, J=0.8, 5.0Hz), 7.44(1H, d, J=2.9Hz), 7.15(1H, dd, J=3.6, 5.0Hz), 5.86(1H, d, J=8.2Hz), 2.80-2.98(1H, m), 2.60-2.80(2H, m), 2.30-2.45(1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; triethylamine;bis(triphenylphosphine)palladium(II)-chloride; copper(I) iodide; In diethyl ether; hexane; dichloromethane; | Step B 2-Trimethylsilylethynylthiophene Under a nitrogen atmosphere a solution of 12.0 grams (0.074 mole) of 2-bromothiophene, 9.0 grams (0.092 mole) of trimethylsilylacetylene, and 120 ml of triethylamine was stirred, and 0.52 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride and 0.28 gram (catalyst) of copper(I) iodide were added. Upon completion of addition, the reaction mixture was stirred at ambient temperature during an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with two portions of an aqueous 10% ammonium chloride solution, one portion of water, and one portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10% methylene chloride in hexane. The appropriate fractions were combined and concentrated under reduced pressure yielding 11.0 grams of 2-trimethylsilylethynylthiophene. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride; In N,N-dimethyl-formamide; at 80℃; for 6h;Inert atmosphere; | General procedure: To a solution of CuCl (50 mg, 0.5 mmol, 50 mol %), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol, 5 mol %), and 4-iodoanisole (2a) (234 mg, 1 mmol) in DMF (5 mL) in a 20 mL of Schlenk tube was added trimethyl(phenylethynyl)silane (1a) (0.39 mL, 2 mmol). The reaction mixture was stirred for 3 h at 80 C, quenched with 1.0 M HCl, and extracted with diethyl ether (20 mL×3). The combined ethereal layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded a dark yellow oil. Column chromatography (silica gel, hexane/diethyl ether=9:1, Rf=0.14) gave the title compound (197 mg, 0.84 mmol, 84% yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With tetrabutyl ammonium fluoride;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; ethanol; at 60℃; for 4.5h;Inert atmosphere; | General Procedure (E)Step B:A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (4.70 mL, 4.7 mmol) and tetrakis(triphenylphosphine)palladium (412 mg, 0.357 mmol) were added to a degassed solution of ethyl [4-[3,3-bis(4-iodophenyl)allylsulfanyl]-2-methylphenoxy]acetate (1010 mg, 1.51 mmol), <strong>[40231-03-6]2-(trimethylsilylethynyl)thiophene</strong> (850 mg, 4.71 mmol; prepared as described in J. Org. Chem. 1996, 61, 6909) and ethanol (0.275 mL, 4.71 mmol) in dry tetrahydrofuran (15 mL). In atmosphere of nitrogen, the resulting mixture was heated to 60 C. for 4.5 h and subsequently cooled down. The solution was diluted with dichloromethane (75 mL) and washed with water (2×20 mL) and brine (2×20 mL). The organic solution was dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexane/ethyl acetate 15:1+0.1% of triethylamine) yielding ethyl [4-[3,3-bis[4-[(thiofen-2-yl)ethylnyl]phenyl]allylsulfanyl]-2-methylphenoxy]acetate as an yellow oil.Yield: 260 mg (27%).M.p. - - - C. (oil).RF (SiO2, hexane/ethyl acetate 90:10) 0.15.1H NMR spectrum (250 MHz, CDCl3, δH): 7.45 (dm, J=8.4 Hz, 2H); 7.40 (dm, J=8.5 Hz, 2H); 7.29 (m, 4H); 7.12 (m, 4H); 7.01 (m, 2H); 6.90 (dm, J=8.3 Hz, 2H); 6.56 (dm, J=9.1 Hz, 1H); 6.18 (t, J=8.0 Hz, 1H); 4.62 (s, 2H); 4.23 (q, J=7.2 Hz, 2H); 3.51 (d, J=7.9 Hz, 2H); 2.22 (s, 3H); 1.26 (t, J=7.2 Hz, 3H). |
27% | With ethanol; tetrabutyl ammonium fluoride;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 60℃; for 4.5h; | General procedure (E); Step B:; A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (4.70 mL, 4.7 mmol) and tetrakis(triphenylphosphine)palladium (412 mg, 0.357 mmol) were added to a de- gassed solution of ethyl [4-[3,3-bis(4-iodophenyl)allylsulfanyl]-2-methylphenoxy]acetate (1010 mg, 1.51 mmol), <strong>[40231-03-6]2-(trimethylsilylethynyl)thiophene</strong> (850 mg, 4.71 mmol; prepared as described in J. Org. Chem. 1996, 61, 6909) and ethanol (0.275 mL, 4.71 mmol) in dry tetra- hydrofuran (15 mL). In atmosphere of nitrogen, the resulting mixture was heated to 60 C for 4.5 h and subsequently cooled down. The solution was diluted with dichloromethane (75 mL) and washed with water (2 x 20 mL) and brine (2 x 20 mL). The organic solution was dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexane/ethyl acetate 15:1 + 0.1 % of triethylamine) yielding ethyl [4-[3,3-bis[4-[(thiofen-2-yl)ethylnyl]phenyl]allylsulfanyl]-2- methylphenoxy] acetate as an yellow oil. Yield: 260 mg (27 %). M. p. No. C (oil). RF (Si02, hexane/ethyl acetate 90: 10) 0.15. ¹H NMR spectrum (250 MHz, CDCl3, No.H) : 7.45 (dm, J=8.4 Hz, 2 H) ; 7.40 (dm, J=8.5 Hz, 2 H); 7.29 (m, 4 H) ; 7.12 (m, 4 H) ; 7.01 (m, 2 H) ; 6.90 (dm, J=8.3 Hz, 2 H) ; 6.56 (dm, J=9.1 Hz, 1 H) ; 6.18 (t, J=8.0 Hz, 1 H) ; 4.62 (s, 2 H) ; 4.23 (q, J=7.2 Hz, 2 H) ; 3.51 (d, J=7.9 Hz, 2 H); 2.22 (s, 3 H) ; 1.26 (t, J=7.2 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
bis(triphenylphosphine)palladium(II)-chloride; In triethylamine; | Step F 2-[5-(4-Trifluoromethylphenylethynyl)thien-2-ylethynyl]benzothiophene This compound was prepared in a manner analogous to that of Example 1, Step B, using 0.5 gram (0.0014 mole) of 2-(5-iodothien-2-ylethynyl)benzothiophene (prepared as in Example 2, Step C), 0.26 gram 0.0015 mole) of 4-trifluoromethylphenylethyne (prepared in Example 2, Step E), and catalytic amounts of bis(triphenylphosphine)palladium(II) chloride and copper (I) iodide in triethylamine. The yield of 2-[5-(4-trifluoromethylphenylethynyl)thien-2-ylethynyl]benzothiophene was 0.25 gram; m.p. 149-150 C. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
copper(I) iodide; In triethylamine; | Step D 2-[2-(4-Trifluoromethylphenyl)thiazol-5-ylethynyl]benzothiophene This compound was prepared in a manner analogous to that of Example 1, Step B, using 1.5 grams (0.04 mole) of 5-iodo-2-(4-trifluoromethylphenyl)thiazole, 0.86 gram (0.005 mole) of 2-ethynylbenzothiophene (prepared as in Example 2, Step C), and catalytic amounts of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in 15 ml of triethylamine. The yield of 2-[2-(4-trifluoromethylphenyl)thiazol-5-ylethynyl]benzothiophene was 1.4 grams; m.p. 178-180 C. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
bis(triphenylphosphine)palladium(II)-chloride; copper(I) iodide; In triethylamine; | Step D 1-(4-Trifluoromethylphenyl)-2-trimethylsilylethyne This compound was prepared in a manner analogous to that of Example 1, Step B, using 17.7 grams (0.0787 mole) of 4-trifluoromethylbromobenzene, 10.9 grams (0.111 mole) of trimethylsilylacetylene, 0.62 gram (0.0009 mole) of bis(triphenylphosphine)palladium(II) chloride and 0.34 gram 0.0018 mole) of copper(I) iodide in triethylamine. The yield of 1-(4-trifluoromethylphenyl)-2-trimethylsilylethyne was 19.8 grams. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
copper(I) iodide; In triethylamine; | Step A 2-Trimethylsilylethynylbenzothiophene This compound was prepared in a manner analogous to that of Example 1, Step B, using 40.9 grams (0.157 mole) of 2-iodobenzothiophene (prepared as in Example 1, Step A), 17.0 grams 0.173 mole) of trimethylsilylacetylene, and catalytic amounts of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in 400 ml of triethylamine. The resulting 2-trimethylsilylethynylbenzothiophene was used in the next reaction without being isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
copper(I) iodide; In triethylamine; | Step D 2-(Thien-2-ylethynyl)benzothiophene This compound was prepared in a manner analogous to that of Example 1, Step B, using 4.2 grams (0.016 mole) of 2-iodobenzothiophene (prepared as in Example 1, Step A), 2.2 grams (0.020 mole) of 2-ethynylthiophene (prepared as in Example 1, Step C), and catalytic amounts of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in 50 ml of triethylamine. The yield of 2-(thien-2-ylethynyl)benzothiophene was 3.5 grams; m.p. 114-116 C. The nmr spectrum was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38%Chromat. | With copper(l) chloride; palladium dichloride; P(p-C6H4F)3; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere; | General procedure: To a solution of PdCl2 (4 mg, 0.02 mmol, 10 mol %), tri(4-fluorophenyl)phosphine (25 mg, 0.08 mmol, 40 mol %), and CuCl (10 mg, 0.1 mmol, 50 mol %) in dry DMF (1 mL) in a 20 mL of Schlenk tube were added an aryl bromide (0.2 mmol) and an alkynylsilane (0.3 mmol) at rt. The reaction mixture was heated at 100 C for 12 h and monitored by GC. GC yields of the corresponding cross-coupled products 3 were determined using heptylbenzene as an internal standard. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; triphenylphosphine; In tetrahydrofuran; at 80℃; for 5h; | General procedure: mp 90-92 C (colorless needles, recrystallized from hexane/THF); Rf: 0.33 (hexane/EtOAc = 4/1); 1H NMR (CDCl3, 400 MHz): 5.88 (s, 1H), 6.91 (d, 2H, J = 8.3 Hz), 7.09 (dd, 1H, J = 3.9, 4.9 Hz), 7.35 (d, 1H, J = 3.9 Hz), 7.36 (d, 1H, J = 4.9 Hz), 7.51 (d, 2H, J = 8.3 Hz); 13C NMR (CDCl3, 100 MHz): .81.3, 92.9, 115.1, 115.5, 123.4, 126.9, 127.0, 131.5, 133.1, 155.7; IR (KBr): vmax 3348, 1604, 1583, 1522, 1501, 1424, 1364, 1342, 1260, 1221, 1171, 1101, 1035, 853, 838, 821 cm-1; HRMS (DART): M+ calcd for C12H8OS, 200.02959; found, 200.03181 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.3 g | To a solution of diisopropylamine (3.4 g, 33.8 mmol) in diethyl ether (20 mL) at -78 C was added dropwise n-butyllithium (19.4 mL, 31.0 mmol, 1.60 M in hexane), and then stirred at -78 C for 15 min. The mixture was warmed to 0 C for 30 min and then re-cooled to -78 C. Trimethyl(thiophen-2-ylethynyl)silane (1) (2.8 g, 15.5 mmol) in diethyl ether (10 mL) at room temperature was then added dropwise to the LDA solution, and the solution was warmed from -78 to 0 C for 15 min. After re-cooling to -78 C, iodine (8.6 g, 33.8 mmol) in diethyl ether (60 mL) was added via cannula, and the solution was then warmed to room temperature and stirred overnight. The mixture was quenched with water, and the aqueous layer was extracted with diethyl ether. The combined organic layer was washed with brine and aqueous sodium thiosulfate, and then dried over magnesium sulfate. The solvent was removed under vacuum, and the crude product was purified by silica column chromatography eluting with petroleum ether to afford compound ((5-iodothiophen-2-yl)ethynyl)trimethylsilane (2) (4.3 g, 90%) as a yellow liquid. The product was used instantly for the next step without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | at 120℃; for 0.166667h;Microwave irradiation; Inert atmosphere; | General procedure: In a microwave reaction vessel, the iodide derivative (0.5mmol, 1.0 eq), PPh3 (5mol%), diethylamine (1.5mmol) and Pd-Cu/C catalyst (5mol% Pd) were suspended in MeOH (3mL). The tube was sealed with a Teflon cap, the reaction mixture was flushed under an argon flow for 5minand then TMSA (1mmol) was added. Then, the reaction mixture was stirred 120C under microwave irradiations for 20min. After completion of the reaction, the azide derivative (0.6mmol) was added and the mixture was irradiated again for 10minat 120C. The mixture was cooled to room temperature, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.61% | With copper(l) iodide; N,N,N',N'',N'''-pentamethyldiethylenetriamine; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 20h; | Example 4 Preparation of 1-phenyl-4-(thiophene-2-yl)-1H-1,2,3-triazole (Formula Ia-vi) A mixture of 2-iodothiophene (500 mg, 2.38 mmol), Pd(PPh3)2Cl2 (52.95 mg, 0.0754 mmol), CuI (28.1 mg, 0.14756 mmol) and diisopropylamine (0.62 ml, 4.4744 mmol) in THF (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.453 ml, 3.284 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield 300 mg of <strong>[40231-03-6]trimethyl(thiophen-2-ylethynyl)silane</strong> (300 mg, 1.66 mol, yield 70.02%). To a solution of <strong>[40231-03-6]trimethyl(thiophen-2-ylethynyl)silane</strong> (50 mg, 0.2777 mmol), phenyl azide (0.5 M solution, 1.1 ml, 0.555 mmol), and CuI (52.87 mg, 0.2777 mmol) in THF (1 ml) was added 1,1,4,7,7-pentamethyldiethlenetriamine (0.116 ml, 0.555 mmol) and 1M TBAF.3H2O (0.554 ml, 0.554 mmol). After stirring the reaction mixture for 20 hours at room temperature, it was quenched with saturated ammonium chloride solution and was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using 5% ethyl acetate in hexane as eluant to yield 1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole (30 mg, 0.132 mol, yield 47.61%) with an HPLC purity of 97.64%. LC-MS [M+H] 228.2 (C12H9N3S+H, expected 228.05). The 1H-NMR spectra was in accordance with the chemical structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; In N,N-dimethyl-formamide; at 50℃; for 4h; | ESEMPIO 2 Preparation of 4, 5-bis (2-ethylhexyloxy) -l-bromo-2- (2- ( 2-thienyl ) ethinyl ) benzene having formula (Ila) The following products were charged, in order, under an inert atmosphere, into a tailed Pyrex glass test-tube equipped with a screw stopper: 540 mg of 4,5- bis ( 2-ethylhexyloxy) -2-bromoiodobenzene (1.0 mmoles) obtained as described in Example 1, 150 mg of 2- [ trimethylsilyl ( ethinyl )] thiophene (0.83 mmoles) (Aldrich) dissolved in 5 ml of N, N-dimethylformamide (Aldrich) , 35 mg of bis ( triphenylphosphine ) - palladium(II) chloride [Pd (PPh3) 2C12] (Aldrich) (0.05 mmoles), 2 mg of copper ( I ) iodide (Cul) (Aldrich) (0.01 mmoles), 304 mg of triethylamine (Aldrich) (3.0 mmoles) and finally 379 mg of tetra-n-butylammonium fluoride (Aldrich) (1.0 mmoles) . After closing the reactor, this was placed in an oil bath preheated to 50C, for 4 hours. After cooling to room temperature (25C) , an aqueous solution of hydrochloric acid 0.1 M (Aldrich) (50 ml) was added to the reaction mixture and the whole mixture was extracted with diethyl ether (Carlo Erba) (3 x 25 ml) . The organic phase obtained was washed to neutrality with water (3 x 25 ml), and subsequently anhydrified on sodium sulfate (Aldrich) and evaporated. The residue obtained was purified by elution on a silica gel chromatographic column [(eluent: heptane) (Carlo Erba) ] , obtaining 425 mg of 4,5-bis(2- ethylhexyloxy) -l-bromo-2- (2- (2-thienyl) ethinyl) benzene as a yellow oil (yield 99%) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In 5,5-dimethyl-1,3-cyclohexadiene; at 200℃; for 24h;Molecular sieve; Inert atmosphere; Sealed tube; | General procedure: A mixture of 0.201g (0.84 mmol) of 2-pyrone 1, 88.6 mg (0.51 mmol) oftrimethyl(phenylethynyl)silane (4a), 0.5 g of powdered MS 4A,and 2 mL of xylene in a sealable pressure vessel was evacuatedand filled with argon. The mixture was heated to 200 C (oil bath) and stirred for 24 h.Upon completion of the reaction, the sealable pressure vessel was cooled to roomtemperature. The reaction mixture was filtered to eliminate the insoluble materials andconcentrated in vacuo. The resulting residue was purified by column chromatography(silica gel, hexane/EtOAc = 15:1) to give the phthalate 5a in quantitative yield (0.189 g,0.51 mmol) as a colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a stirring solution of alkyne 7 (30 g 0.17 mol, 2.7 equiv.) in 1.2 l of dry toluene at r.t. under a N2 atmosphere was added Ti(Oi-Pr)4 (49.1 g, 0.17 mmol2.7 equiv.). The resulting mixture was cooled to -78 C and n-BuLi (2.7 M, 135 ml, 0.364 mol, 5.7 equiv.) was added dropwise. The resulting black mixture was warmed first to r.t., then heated to 50 C and stirred at that temperature for 1 h (no reflux condenser required). In a separate flask under a N2 atmosphere, enyne ent-6 (14.7 g,0.064 mol, 1.0 equiv.) was dissolved in 300 ml of dry toluene, cooled to -78 C and treated with n-BuLi (2.5 M, 25 ml, 0.064 mmol, 1.0 equiv.), and added dropwise at-78 C. The resulting mixture was warmed to r.t. and then transferred by cannula to the black Ti-alkyne complex at -78 C. The mixture was slowly warmed to r.t. overnight (∼17 h). After this period, 1.5 l of dry MeOH was cooled to -78 C in aseparate flask under a N2 atmosphere and the reaction mixture was transferred by cannula to the pre-cooled MeOH. Once the addition was complete, the reaction mixture was warmed to r.t. and 500 ml of deionized H2O was added. A 500 ml volume of EtOAc was added, the organic phase was separated, and the aqueous layerwas extracted with EtOAc (500 ml × 3). The combined organic layers were dried over MgSO4, the drying agent was removed by filtration, and the resulting solution was concentrated in vacuo. Purification of the crude product by flash column chromatography afforded 12.4 g of the title hydrindane ent-8 as a yellow film (60%, isolated as a 4:1 mixture of ent-8:ent-9). | ||
To a stirring solution of alkyne 31 (2.4 g, 13 mmol, 3.0 equiv) in 80 mL of dry toluene at rt under N2 atmosphere was added Ti(0/'-Pr)4 (3.7 g, 13 mmol 3.0 equiv). The resulting mixture was cooled to -78 C, and n-BuLi (2.4 M in hexanes, 1 1 mL, 26 mmol, 6.0 equiv) was added dropwise. The resulting black Ti-alkyne complex was warmed first to rt, then heated to 50 C and stirred at 50 C for 1 h (a reflux condenser was not used). In a separate flask, under N2 atmosphere, enyne ent-6 (1 .0 g, 4.3 mmol, 1 .0 equiv) was dissolved in 20 mL of dry toluene, cooled to -78 C, and then n-BuLi (2.4 M in hexanes, 1 .8 mL, 4.3 mmol, 1 .0 equiv) was added dropwise. The resulting yellow solution was warmed to rt, and then transferred by cannula to the black Ti-alkyne complex at -78 C. The mixture was slowly warmed to rt overnight (approx. 17 h). After this period, 80 mL of dry MeOH in a separate flask was cooled to -78 C under N2 atmosphere, and the reaction mixture was transferred by cannula to the pre-cooled MeOH. Once the addition was complete, the reaction mixture was warmed to rt, and 70 mL of sat. NaHC03 (aq) was added. The reaction mixture was further diluted with 100 mL Et20. The organic layer was separated, and the aqueous layer was extracted with Et20 (100 mL χ 2). The combined organic layers were dried over anhydrous Na2S04, filtered through a coarse fritted glass funnel, and then the filtrate was concentrated in vacuo. Purification of the crude product by flash column chromatography afforded 0.69 g of compounds hydrindane 32 and S14 as a yellow oil (49%, isolated as a 5:1 mixture of 32:S14). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene; at 65℃; for 96h; | General procedure: (COD)Ni(dippe) (56 mg,0.130 mmol) and tris(trimethylsilyl)silylethyne (2) (36 mg, 0.130 mmol) were dissolved in toluene(3 mL) and stirred for 4 d at 65 C. The progress of the reaction was checked by NMR. After removingthe solvent dark green crystalline 2c (59 mg, 85%) was obtained. |
Tags: 40231-03-6 synthesis path| 40231-03-6 SDS| 40231-03-6 COA| 40231-03-6 purity| 40231-03-6 application| 40231-03-6 NMR| 40231-03-6 COA| 40231-03-6 structure
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