Structure of 23055-10-9
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CAS No. : | 23055-10-9 |
Formula : | C6H8O4 |
M.W : | 144.13 |
SMILES Code : | O=C(OC)/C=C/C(OC)=O |
MDL No. : | MFCD00064438 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H313-H317-H319-H335-H373-H401 |
Precautionary Statements: | P260-P264-P270-P271-P272-P273-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P312-P333+P313-P337+P313-P403+P233-P405-P501 |
* 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 |
---|---|---|
75% | In acetone; for 1h;Inert atmosphere; | General procedure: 0.0813 g (0.4637mmol) of TMQ, 0.1671 g (1.159 mmol) of dmfu and 0.2000 g (0.1932 mmol) of [Pd2(DBA)3. CHCl3] were dissolved under inert atmosphere (Ar) in 30 ml of anhydrous acetone. The mixture was stirred for 60 m and eventually treated with active charcoal for 5/10 min and filtered on celite filter. The resulting yellow solution was dried under vacuum and the residual treated with diethyl ether, filtered, washed with diethyl ether in excess and dried under vacuum. 0.1104 g (yield 67percent) of the title compound was obtained as pale yellow microcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In acetone; for 1h;Inert atmosphere; | 0.0813 g (0.4637mmol) of TMQ, 0.1671 g (1.159 mmol) of dmfu and 0.2000 g (0.1932 mmol) of [Pd2(DBA)3. CHCl3] were dissolved under inert atmosphere (Ar) in 30 ml of anhydrous acetone. The mixture was stirred for 60 m and eventually treated with active charcoal for 5/10 min and filtered on celite filter. The resulting yellow solution was dried under vacuum and the residual treated with diethyl ether, filtered, washed with diethyl ether in excess and dried under vacuum. 0.1104 g (yield 67percent) of the title compound was obtained as pale yellow microcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In acetone; for 1h;Inert atmosphere; | 0.1127g (0.4871mmol) of Me-TtBQ, 0.1755g (1.218mmol) of dmfu and 0.2101g (0.2030mmol) of [Pd2(DBA)3·CHCl3] were dissolved under inert atmosphere (Ar) in 30ml of anhydrous acetone. The mixture was stirred for 60min and eventually treated with active charcoal for 5/10min and filtered on Celite filter. The resulting yellow solution was dried under vacuum and the residual treated with diethyl ether, filtered off, washed with diethyl ether in excess and dried under vacuum. 0.1452g (yield 75percent) of the title compound was obtained as pale yellow microcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In acetone; for 1h;Inert atmosphere; | General procedure: 0.1127g (0.4871mmol) of Me-TtBQ, 0.1755g (1.218mmol) of dmfu and 0.2101g (0.2030mmol) of [Pd2(DBA)3·CHCl3] were dissolved under inert atmosphere (Ar) in 30ml of anhydrous acetone. The mixture was stirred for 60min and eventually treated with active charcoal for 5/10min and filtered on Celite filter. The resulting yellow solution was dried under vacuum and the residual treated with diethyl ether, filtered off, washed with diethyl ether in excess and dried under vacuum. 0.1452g (yield 75%) of the title compound was obtained as pale yellow microcrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With copper (II)-fluoride; triphenylphosphine; In 1,1,2-trichloroethane; 1,2-dichloro-ethane; at 80℃; for 24h;Green chemistry; | The reaction flask was charged with CuF2 (0.6 mmol, 60 mg), PPh3 (0.6 mmol, 157 mg), Compound 1a (9 mmol, 1287 mg), Compound 2a (3 mmol, 432 mg), compound 3a (9 mmol, 1026 mg), 1,2-dichloroethane (5.0 mL), 1,1,2-trichloroethane (5.0 mL). The system was then heated in air at 80 ° C for about 24 hours, washed with 1 mol / L hydrochloric acid solution, extracted with dichloromethane (40 mL x 3), adsorbed on silica gel. The product 4f was obtained by a simple column chromatography in 69percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With copper (II)-fluoride; In 1,1,2-trichloroethane; 1,2-dichloro-ethane; at 80℃; for 24h;Green chemistry; | The reaction flask was charged with CuF2 (0.6 mmol, 60 mg), compound 5e(9 mmol, 1161 mg), Compound 2a (3 mmol, 432 mg), compound 3a (9 mmol, 1026 mg), 1,2-dichloroethane (5.0 mL), 1,1,2-trichloroethane (5.0 mL). The system was then heated in air at 80 C for about 24 hours, washed with 1 mol / L hydrochloric acid solution, extracted with dichloromethane (40 mL x 3), adsorbed on silica gel. The product 6ewas obtained by a simple column chromatography in a yield of 67%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In acetone; for 1h;Inert atmosphere; | 0.1624 g (0.4076 mmol) of 1,2-bis(diphenylphosphine)ethane, 0.1671 g (1.159 mmol) of dmfu and 0.2002 g (0.1934 mmol) of [Pd2(DBA)3*CHCl3] were dissolved under inert atmosphere (Ar) in 30 ml of anhydrous acetone and vigorously stirred for 60 min. Owing to the progressive dissolution of [Pd2(DBA)3*CHCl3], the violet color of the mixture gradually disappeared and the concomitant precipitation of the scarcely soluble pale yellow complex 1j was observed. The solution was dried under vacuum, the residue dissolved in CH2Cl2, treated with activated charcoal and filtered on a celite filter. The clear pale yellow solution was concentrated under vacuum and the title complex precipitated by slow addition of diethylether. Complex 1j was filtered off on a gooch, washed with diethylether and dried under vacuum. 0.2027 g (yield 81percent) of the title complex 1j as a pale yellow solid was obtained. 1H NMR (300 MHz, CDCl3, T = 298 K, ppm) delta: 2.11-2.61 (m, 4H, CH2P), 3.40 (s, 3H, OCH3), 4.33-4.42 (m, 2H, CH=CH), 7.32-7.53 (m, 16H, PPh), 7.79-7.85 (m, 4H, PPh). 13C{1H} NMR (CDCl3, T = 298 K, ppm selected peaks) delta: 26.7 (m CH2, CH2P), 50.5 (CH3, OCH3), 52.9 (m, CH, CH=CH), 173.7 (C, CO). 31P{1H} NMR (CD2Cl2, T = 298 K, ppm) delta: 39.0. IR (KBr, pellet, cm-1): 1683 (nCO). Anal. Calcd. for C32H32O4P2Pd: C 59.22, H 4.97. Found: C 59.11, H 5.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In acetonitrile; at 50℃; | dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile was added.0.275 mmol of dimethyl butenedioate,The reaction was carried out under the conditions of Table 1. After the reaction was completed, it was cooled to room temperature.Add water and extract three times with ethyl acetate.Dried over anhydrous magnesium sulfate,The solvent was removed by filtration under reduced pressure.Separated and purified by column chromatography,Get the product,The column chromatography eluate used was a petroleum ether:ethyl acetate mixed solvent in a volume ratio of 10:1 to 5:1. |