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CAS No. : | 657-84-1 | MDL No. : | MFCD00064388 |
Formula : | C7H7NaO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KVCGISUBCHHTDD-UHFFFAOYSA-M |
M.W : | 194.18 | Pubchem ID : | 3720192 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.42 |
TPSA : | 65.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.77 cm/s |
Log Po/w (iLOGP) : | -7.71 |
Log Po/w (XLOGP3) : | 1.0 |
Log Po/w (WLOGP) : | 1.98 |
Log Po/w (MLOGP) : | 1.45 |
Log Po/w (SILICOS-IT) : | 0.64 |
Consensus Log Po/w : | -0.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.98 |
Solubility : | 2.04 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.97 |
Solubility : | 2.1 mg/ml ; 0.0108 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.13 |
Solubility : | 1.44 mg/ml ; 0.00741 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.84 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
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 |
---|---|---|
46% | In acetonitrile; at 80℃; for 17h; | Example 57 (956 mg, 0.998 mmol) was dissolved in acetonitrile (20 ml) and <strong>[657-84-1]sodium tosylate</strong> (290 mg, 1.50 mmol) was added. The reaction mixture was heated at 80sC under argon for 17 h. After cooling, the solid was filtered off and the filtrate was evaporated. The product was purified on an Isolute Al-N cartridge (10 g) eluting with 0-6% MeOH in DCM, and obtained as a cream solid. Yield: 5.03 (46%)LC-MS ((Method 3): Rt = 7.97 min, m/z = 922.38 [M]+1 H NMR (400 MHz, DMSO-d6): d = 1.71 (br m, 4H); 2.24 (s, 3H); 2.82 (s, 6H); 2.99- 3.30 (m, 8H); 3.81 (s, 4H); 5.40 (d, 2H); 7.10 (d, 2H); 7.43 (d, 2H); 7.61-7.90 (m, 16H); 8.21 (d, 2H) ppm. |
46% | In acetonitrile; at 80℃; for 17h; | Example 57 (956 mg, 0.998 mmol) was dissolved in acetonitrile (20 ml) and <strong>[657-84-1]sodium tosylate</strong> (290 mg, 1.50 mmol) was added. The reaction mixture was heated at 80QC under argon for 17 h. After cooling, the solid was filtered off and the filtrate was evaporated. The product was purified on an Isolute Al-N cartridge (10 g) eluting with 0-6% MeOH in DCM, and obtained as a cream solid. Yield: 5.03 (46%)LC-MS ((Method 3): Rt = 7.97 min, m/z = 922.38 [M]+1 H NMR (400 MHz, DMSO-d6): delta = 1.71 (br m, 4H); 2.24 (s, 3H); 2.82 (s, 6H); 2.99- 3.30 (m, 8H); 3.81 (s, 4H); 5.40 (d, 2H); 7.10 (d, 2H); 7.43 (d, 2H); 7.61-7.90 (m, 16H); 8.21 (d, 2H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.83% | In water; | b) Preparation of p-methoxy cinnamidopropyldimethyllauryl ammonium tosylate p-Methoxy cinnamidopropyldimethyllauryl ammonium chloride (17.78 g, 38.11 mmol) was dissolved in water (60 ml) to make 30% solution. To this stirred solution, sodium p-toluene sulphonate (7.4 g, 38.14 mmol) was added and the separated pale yellow coloured solid was subsequently washed with water, filtered and dried to yield the corresponding tosylate (22.9 g, 99.83%) as off-white solid, m.p. 128-130 C. Chloride ion was totally absent in the product. IR (CH2Cl2): 3465, 3286, 3052, 2920, 1659, 1617 cm-1 . 1H NMR (CDCl3, 300 MHz): delta 0.87 (3H, t, J=6.3 Hz), 1.18 (18H, broad signal), 1.58 (2H), unresolved multiplet), 2.10 (2H, unresolved multiplet), 2.32 (3H, singlet, methyl of tosyl), 3.13 (6H, singlet, two methyl on nitrogen), 3.20 (2H, unresolved multiplet), 3.45 (2H, unresolved multiplet), 3.68 (2H, unresolved multiplet), 3.78 (3H, singlet, OCH3), 6.52 (1H, d, J=15.6 Hz), 6.76 (2H, d, J=8.4 Hz), 7.14 (2H, d, J=6.0 Hz), 7.31 (2H, d, J=8.6 Hz), 7.48 (1H, d, J=15.6 Hz), 7.78 (2H, d, J=7.8 Hz). 13C NMR (125 MHz, CDCl3): delta 14.10, 21.27, 22.69, 26.35, 29.23, 29.34, 29.51, 29.64, 31.93, 36.38, 50.67, 55.24, 62.47, 64.24, 114.10, 119.43, 125.83, 127.92, 128.89, 129.47, 139.56, 143.87, 160.67, & 167.25. The molar extinction coefficient, epsilon was found to be 25,000 at lambdamax 310 nm in methanol. The final compound was analysed on HPLC using ion-pairing technique. The mobile phase employed for ion-pairing comprised of 0.1 M octane sulphonic acid in aqueous methanol (80:30). Reversed phase column Chromspher C8 was used with mobile phase flow rate of 1.0 ml/min. The detection was done at 280 nm. The purity of final compound from this analysis was found to be 99.9%. The spectral and chromatographic data were in total agreement with the reported values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.93% | In water; | b) Preparation of p-N,N-dimethylamino benzamidopropyl dimethyl lauryl ammonium chloride tosylate p-N,N-Dimethylamino benzamidopropyldimethyllauryl ammonium chloride (5.455 g, 12.03 mmol) was dissolved in water to make 30% solution. To this stirred solution, sodium p-toluene sulphonate (2.34 g, 12.06 mmol) was added and the separated pale yellow coloured solid was subsequently washed with water, filtered and dried to yield the corresponding tosylate (7.08 g, 99.93%) as pale yellow coloured solid. Chloride ion was totally absent in the product. The spectral data (UV, IR and 1H NMR) was found to be identical with the one obtained by literature route. Reversed phase HPLC showed it to be 99.9% pure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; Phthalic acid dibutyl ester; water; at 90℃; for 0.25 - 3h;Conversion of starting material; | Methyl methanesulfonate (MMS), methyl para-toluenesulfonate (MTS), butyl methanesulfonate (BMS), or <strong>[778-28-9]butyl para-toluenesulfonate</strong> (BTS) was combined with either dimethyl phthalate (DMP) or dibutyl phthalate (DBP) to obtain initial mixtures with 55-148 ppm (w/w) sulfonate ester as tabulated below. The mixtures were then heated with vigorous stirring to 180 C., then cooled to 90 C. to simulate general esterification conditions. After such preparation, the resulting mixtures would have compositions similar to those observed in crude esterification product mixtures from typical commercial manufacturing processes. An aliquot of each mixture was taken at this point to represent the material prior to hydrolysis (i.e., time ?0?). The hydrolysis medium was then added (30 ml water, aqueous 10% NaOH, or aqueous 10% Na2CO3) and the stirred mixture was maintained at 90 C. Aliquot samples were taken at the times specified in the table below. Each aliquot was extracted with diethyl ether, and the ether extracts washed with water, dried, and evaporated under vacuum to obtain the dry phthalate ester with residual sulfonate ester. The latter were then analyzed by gas chromatography to determine the amount of residual sulfonate ester. Initial Residual Sulfonate ester (ppm Sulfonate ester by weight) in Phthalate ester Phthalate Sulfonate Before Heating Hydrolysis after Hydrolysis Time (min.) Ester Ester (ppm w/w) Medium 0 15 30 60 120 180 DMP 200 ml MMS 55 Water 34 15 10 5.2 1.3 DMP 200 ml MTS 95 Water 101 98 93 93 83 DBP 200 ml BMS 55 Water 51 35 34 31 23 DBP 200 ml BTS 84 Water 81 78 76 76 72 DMP 100 ml MMS 136 Aq. NaOH 68 4 - <1 <1 - DMP 200 ml MTS 97 Aq. NaOH 70 64 53 40 24 DBP 200 ml BMS 48 Aq. NaOH 18 13 - 14 10 - DBP 200 ml BTS 84 Aq. NaOH 61 59 59 54 55 DMP 100 ml MMS 148Aq. Na2CO3 - 3 - <1 <1 - DBP 100 ml BMS 96Aq. Na2CO3 30 33 - 31 17 - |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In water; | Preparation of p-methoxy cinnamidopropyldimethylbehenyl ammonium tosylate; p-Methoxy cinnamidopropyldimethylbehenyl ammonium chloride (115 g, 190 mmol) was dissolved in water (300 ml) to make 35% solution. To this stirred solution, sodium p-toluene sulphonate (37 g, 190 mmol) was added and the separated pale yellow coloured solid was subsequently washed with water, filtered and dried to yield the corresponding tosylate (131 g, 93%) as off-white solid, m.p. 50-55 C. Chloride ion was totally absent in the product. The molar extinction coefficient, epsilon was found to be 23,000 at lambdamax 305 nm in methanol. IR (CH2Cl2): 3300, 1664 cm-1. 1H NMR (CDCl3, 300 MHz): delta 0.87 (3H, t, J=6.3 Hz), 1.18 (34H, broad signal), 1.58 (2H, unresolved multiplet), 2.10 (2H, unresolved multiplet), 2.32 (3H, singlet, methyl of tosyl), 3.13 (6H, singlet, two methyl on nitrogen), 3.20 (2H, unresolved multiplet), 3.45 (2H, unresolved multiplet), 3.68 (2H, unresolved multiplet), 3.78 (3H, singlet, OCH3), 6.52 (1H, d, J=15.6 Hz), 6.76 (2H, d, J=8.4 Hz), 7.14 (2H, d, J=6.0 Hz), 7.31 (2H, d, J=8.6 Hz), 7.48 (1H, d, J=15.6 Hz), 7.78 (2H, d, J=7.8 Hz). The p-methoxy cinnamidopropyldimethylbehenyl ammonium tosylate was analysed on HPLC using ion-pairing technique. The mobile phase employed for ion-pairing comprised of 0.1 M octane sulphonic acid in aqueous methanol (80:30). Reversed phase column Chromspher C8 was used with mobile phase flow rate of 1.0 ml/min. The detection was done at 280 nm. The purity of final compound from this analysis was found to be 99.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In water; for 0.0025h;Heating / reflux; | b) Preparation of p-N,N-dimethylamine benzamidopropyldimethylbehenyl ammonium tosylate; p-N,N-dimethylamino benzamidopropyldimethylbehenyl ammonium chloride (23 g, 39 mmol) was dissolved in water (50 ml) to make 30% solution. To this stirred solution, sodium p-toluene sulphonate (8 g, 41 mmol) was added and the separated pale yellow coloured solid upon heating on a water-bath for 0.15 minutes was subsequently washed with water, filtered and dried to yield the corresponding tosylate (26 g, 93%) as off-white solid, m.p. 54-57 C. Chloride ion was totally absent in the product. The molar extinction coefficient, epsilon was found to be 22,200 at lambdamax 305 nm in methanol. IR (CH2Cl2): 1608, 1636, 3427 cm-1. 1H NMR (CDCl3, 300 MHz): delta 0.88 (3H, t, J=6.3 Hz), 1.06-1.44 (40H, broad signal), 2.01 (2H, unresolved multiplet), 2.30 (3H, s, methyl of tosyl), 2.91 (6H, s), 3.01 (6H, s), 3.06 (2H, unresolved multiplet), 3.44 (1H, s), 3.46 (2H, t), 3.65 (2H, t), 6.47 (2H, d, J=8.7 Hz), 7.11 (2H, d, J=8.1 Hz), 7.73 (2H, d, J=8.1 Hz), 7.83 (2H, d, J=9.3 Hz). The final compound was analysed on HPLC using ion-pairing technique. The mobile phase employed for ion-pairing comprised of 0.1 M octane sulphonic acid in aqueous methanol (90:10). Reversed phase column Chromspher C8 was used with mobile phase flow rate of 1.0 ml/min. The detection was done at 280 nm. The purity of final compound from this analysis was found to be 99.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.5 - 45% | With formic acid; In methanol; at 20℃; for 1.16667h; | Intermediate K Trans-2-[tert-Butoxycarbonylamino-(toluene-4-sulfonyl)-methyl]-cyclopropanecarboxylic acid ethyl ester 2-Formyl-cyclopropanecarboxylic acid ethyl ester (88-90% trans isomer) (2.9 g, 20.4 mmol) was solved in methanol and 2.4 g (20.49 mmol) of tert-butylcarbamate was added followed by sodium p-toluensulfinate in water (40 mL). After stirring at room temperature 5 mL (132.5 mmol) of formic acid was added and the mixture was stirred for 70 minutes until the product precipitated. The solid was filtrated and washed with water and heptane and dried under high vacuum to obtain 3.6 g. (44.5% yield) of the title compound (only the trans isomer) as a white solid. MS (m/e): 384.5 (M+H+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With hydrogenchloride; In diethyl ether; water; for 0.5h; | H20 (10 ml) was added to p-toulenesulfinic acid sodium salt (2.00 g, 10.3 mmol), and the resulting mixture was stirred for 30 min until a clear solution was obtained. Diethyl ether (10 ml) was added, followed by cone. HCI (0.7 ml) and stirring was continued for an additional 30 min. The organic layer was separated, diluted with toluene (10 ml) and concentrated on the rotary evaporator until around 90% of the solvent was removed. Heptane (5 ml) was added and the white solid obtained was filtered, washed with heptane and dried under vacuum to give to p-toulenesulfinic acid as a white solid (1 .1 g, 69%). 1 H NMR (DMSO-d6, 400 MHz) delta 2.37 (3 H, s), 7.36 (1 H, d, J = 8 Hz), 7.54 (1 H, d, J = 8 Hz); 13C NMR (DMSO-d6, 100 MHz) delta 20.9, 124.5, 129.4, 141 .3, 146.0. |
Isolation of p-tolylsulfinic acid: Sodium p-tolylsulfinate (anhydrous) (3.21 g, 18.0 mmol) was suspended in water (25 mL). After stirring for 10 minutes, all was dissolved and £-butylmethylether (TBME) (25 mL) was added. Then, concentrated HCI (aq) (1.6 mL, 1 eq) was added dropwise. After stirring for 20 minutes, the organic phase was separated, diluted with toluene (25 mL), and evaporated in vacuo to remove 70-90% of the solvents. Heptane (7 mL) was added to the resulting slurry, and the precipitate was isolated on a glass filter, washed with heptane, and dried in vacuo. The resulting crude p-tolylsulfinic acid was used fresh in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90%Spectr. | With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 4h; | General procedure: To a solution of 1 or 2 (0.30 mmol, 1.0 equiv.) in dry DCM (1 mL) were added cyclohexene (3) (0.30 mmol, 1.0 equiv.) and <strong>[657-84-1]sodium tosylate</strong> (0.45 mmol, 1.5 equiv.). The resulting suspension was vigorously stirred at room temperature. After stirring for 5 min, the Lewis acid (1.5 mmol, 5.0 equiv.) was added dropwise. The resulting mixture was stirred at the defined temperature for 4 h. The reaction mixture was then partitioned between Et2O and H2O, the organic phase was washed with aqueous HCl (2 M), dried over Na2SO4 and filtered. After removing solvent in vacuo, the crude was purified by flash chromatography to afford the desired product 4.5. (1R*,2R*)-2-[(trifluoromethyl)sulfanyl]cyclohexyl 4-methylbenzene-1-sulfonate (4a). Eluent for the flash chromatography: pentane/acetone: 70/1. 1H NMR: delta = 7.80 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.1 Hz, 2H), 4.49 (td, J = 6.6 Hz, 3.6 Hz, 1H), 3.29 (td, J = 6.9 Hz, 4.2 Hz, 1H), 2.44 (s,3H), 2.22 (m, 1H), 2.03 (m, 1H), 1.69-1.65 (m, 3H), 1.48-1.44 (m,3H). 19F NMR: delta = -40.06 (s, 3F). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | General procedure: Alkynyliodonium salt 1a-g (1 mmol, 1 equiv) and CsF (76 mg, 0.5 equiv) were dissolved in a mixture of acetonitrile (4 mL) and water (40 muL). The reaction solution was stirred at 60 C for 1 h, cooled at room temperature and was poured onto a solution of NaBF4 (for 1a,c-f) or NaOTs (for 1b,g) (5% in water, 10 mL). The resulting mixture was stirred for additional 10 min and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to give the corresponding fluoroalkenyliodonium salts 2a-g, which were purified by column chromatography on silica gel (CH2Cl2/MeOH: 90/10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | General procedure: Alkynyliodonium salt 1a-g (1 mmol, 1 equiv) and CsF (76 mg, 0.5 equiv) were dissolved in a mixture of acetonitrile (4 mL) and water (40 muL). The reaction solution was stirred at 60 C for 1 h, cooled at room temperature and was poured onto a solution of NaBF4 (for 1a,c-f) or NaOTs (for 1b,g) (5% in water, 10 mL). The resulting mixture was stirred for additional 10 min and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to give the corresponding fluoroalkenyliodonium salts 2a-g, which were purified by column chromatography on silica gel (CH2Cl2/MeOH: 90/10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 100℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32%; 5% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 100℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper dichloride; palladium dichloride; In 1,4-dioxane; at 90℃; for 8h; | General procedure: A mixture of sulfinic acid sodium salt (0.60 mmol), PdCl2 (0.10 equiv), Baylis Hillman aduct (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10 mL RB flask. The mixture was vigorously stirred at 90 C for 8 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (25.0 mL) and water (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane and ethyl acetate (eluent system) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol; water; at 50 - 55℃; for 1h; | Synthesis of Color Material J10179] First, 1.15 g (5.94 mmol) of Sodium p-toluenesulfonate (manufactured by: Tokyo Chemical Industry Co., Ltd.), 33 mE of methanol and 33 mE of water were mixed and agitated at 50 to 55 C. Next, 3.19 g (2.97 mmol) ofintermediate 2 was added thereto, and the mixture was agitated at 50 to 55 C. for 1 hour. The solution was concentrated by means of an evaporator to evaporate the methanol, and 100 mE of water was added thereto. The mixture was filtered to obtain a precipitate, and the precipitate was washed with watet The thus-obtained cake was dried to obtain 3.33 g (yield 83%) of color material J represented by the following chemical formula (14).10180] From the following analysis result, the obtained compound was confirmed to be a desired compound.j0181] MS (ESI) (mlz): 502(+), divalent, 171(-), monovalent10182] Values of elemental analysis: CHN actual measurement values (75.18%, 7.11%, 6.15%); theoretical values (74. 97%, 6.89%, 6.24%) |
83% | In methanol; water; at 50 - 55℃; for 1h; | Example 2Synthesis of Color Material BFirst, 1.15 g (5.94 mmol) of sodium p-toluenesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd.), 33 mL of methanol, and 33 mL of water were mixed and agitated at 50 to 55 C. Then, 3.19 g (2.97 mmol) of the color material A obtained in Example 1 was added to the mixture, and the mixture was agitated for one hour at 50 to 55 C. The methanol in the solution was evaporated with an evaporator. Then, 100 mL of water was added thereto, and a precipitate thus obtained was collected by filtration and washed with water. The thus-obtained cake was dried, thereby obtaining 3.33 g (yield 83%) of the color material B represented by the following chemical formula (3).From the following analysis result, the obtained compound was confirmed to be a desired compound.MS(ESI) (m/z): 502(+), divalent, 171(-) monovalentValues of elemental analysis: CHN actual measurement values (75.18%, 7.11%, 6.15%); theoretical values (74.97%, 6.89%, 6.24%) |
83% | In water; toluene; at 50 - 55℃; for 1h; | Add to the Tokyo Chemical Industry-made p-toluenesulfonate 1.15 g (5.94Mmol, 33 mL of toluene and 33 mL of water at 50-55 C. add3.19 g (2.97 mmol) of colorant A obtained in Example 1 was added at 50-55 CFollowed by stirring for 1 hour. The alcohol in the solution was concentrated and added by an evaporatorWater 100 mL and filter, take Shen Tong things, with water for cleaning. The cake was dried(Yield 83%) of color material B represented by the following chemical formula (3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; at 100℃; for 42h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With [2,2]bipyridinyl; copper(l) iodide; lithium chloride; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With [2,2]bipyridinyl; copper(l) iodide; potassium iodide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 80℃; for 18h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 1,3-dimethyl-2-imidazolidinone; copper(l) chloride; (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With 1,3-dimethyl-2-imidazolidinone; copper(l) chloride; (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With 1,3-dimethyl-2-imidazolidinone; copper(l) chloride; (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine; In water; acetic acid; at 60℃; for 36h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1,3-dimethyl-2-imidazolidinone; copper(l) chloride; (S,S)-N,N'-bis(p-tolylsulfonyl)-trans-cyclohexane-1,2-diamine; In water; acetic acid; at 60℃; for 66h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With [2,2]bipyridinyl; copper(l) iodide; lithium chloride; In acetic acid; at 100℃; for 36h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With [2,2]bipyridinyl; copper(l) iodide; potassium iodide; In acetic acid; at 100℃; for 36h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With [2,2]bipyridinyl; copper(l) iodide; potassium bromide; In acetic acid; at 100℃; for 36h; | General procedure: 4.3 Typical procedure for copper-catalyzed synthesis of beta-haloalkenyl sulfone (Table 4): To a mixture of CuI (4.6 mg, 0.024 mmol), bpy (3.7 mg, 0.024 mmol), PhSO2Na (54.2 mg, 0.33 mmol), and KBr (107.1 mg, 0.9 mmol) in AcOH (0.3 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 80 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with saturated sodium hydrogencarbonate, H2O, and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-2-bromo-1-phenylsulfonyl-2-phenylethene (71.5 mg, 74%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With 1,3-dimethyl-2-imidazolidinone; 4,4?,5,5?-Tetrahydro-2,2?-bioxazole; copper(l) chloride; In water; acetic acid; at 60℃; for 18h; | General procedure: 4.2. Typical procedure hydrosulfonylation of alkynes (Table 2 ): To a mixture of CuCl (1.5 mg, 0.015 mmol), 2,2'-bis(2-oxazoline) (2.1 mg, 0.015 mmol), and PhSO2Na (54.2 mg, 0.33 mmol), in DMI (0.1 mL), H2O (0.1 mL), and AcOH (0.1 mL) were added phenylacetylene (30.6 mg, 0.3 mmol), and the mixture was stirred at 60 C for 18 h in air. After the residue was dissolved in Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (40% diethyl ether/hexane) gave (E)-1-phenylsulfonyl-2-phenylethene (61.8 mg, 85%):1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: A solution of carbohydrate alkyne (1 mmol), sulfonyl azide[2] (1 mmol), CuI (0.1 mmol) and salisaldehyde or o-hydroxy acetophenone (1.1 mmol) in dry THF (5 mL) in a 25 mL round bottomed flask was stirred under nitrogen for 1 hour. Et3N (2 mmol) was then added slowly via syringe. The resulting solution was allowed to stir at room temperature for 12 hours when TLC showed complete conversion of the starting carbohydrate alkyne (n-hexane-EtOAc). Solvents were evaporated in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and washed successively with aqueous NH4Cl (210 mL) and brine (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography using n-hexane-EtOAc as eluent to afford pure glycosylated N-sulfonyl iminocoumarins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85%Spectr. | With boron trifluoride diethyl etherate; In dichloromethane; at 50℃; for 4h; | General procedure: To a solution of 1 or 2 (0.30 mmol, 1.0 equiv.) in dry DCM (1 mL) were added cyclohexene (3) (0.30 mmol, 1.0 equiv.) and <strong>[657-84-1]sodium tosylate</strong> (0.45 mmol, 1.5 equiv.). The resulting suspension was vigorously stirred at room temperature. After stirring for 5 min, the Lewis acid (1.5 mmol, 5.0 equiv.) was added dropwise. The resulting mixture was stirred at the defined temperature for 4 h. The reaction mixture was then partitioned between Et2O and H2O, the organic phase was washed with aqueous HCl (2 M), dried over Na2SO4 and filtered. After removing solvent in vacuo, the crude was purified by flash chromatography to afford the desired product 4.5. (1R*,2R*)-2-[(trifluoromethyl)sulfanyl]cyclohexyl 4-methylbenzene-1-sulfonate (4a). Eluent for the flash chromatography: pentane/acetone: 70/1. 1H NMR: delta = 7.80 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.1 Hz, 2H), 4.49 (td, J = 6.6 Hz, 3.6 Hz, 1H), 3.29 (td, J = 6.9 Hz, 4.2 Hz, 1H), 2.44 (s,3H), 2.22 (m, 1H), 2.03 (m, 1H), 1.69-1.65 (m, 3H), 1.48-1.44 (m,3H). 19F NMR: delta = -40.06 (s, 3F). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In water; at 20℃; for 4h;Inert atmosphere; | In a 2 L four-necked flask equipped with a stirrer and a nitrogen gas inlet tube, 301.7 g (1.12 g) of 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium chloride Mol), ion exchanged water (300.3 g) and sodium paratoluenesulfonate (222.05 g, 1.43 mol), and the mixture was stirred at room temperature for 4 hours. After completion of stirring, the reaction solution was concentrated with a rotary evaporator. The obtained concentrate was dissolved with 264.96 g of acetonitrile, and the resulting white precipitate was separated by filtration. The filtrate was placed in a rotary evaporator and concentrated, then the concentrate was dried in vacuo to give 3-benzyl-5- (2-hydroxyethyl) -4-methylthiazolium = paratoluenesulfonate362.3 g were obtained (yield: 98percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In methanol; at 60℃; for 1h; | General procedure: The sodium benzenesulfonates (2a-c) (2mmol) with crown ethers (1a, 1b) (2mmol) in 15 mL methanol were stirred for 1 h at 60C. Then methanol was removed under reduced pressure. The residue was vacuum dried to generate the desired CECIL in 100% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Under ice-cooling conditions, 10 g of <strong>[58101-60-3]methyl 3-cyclopentene-1-carboxylate</strong> and 21.2 g of sodium p-toluenesulfinate were weighed and placed in a reaction flask, and 500 mL of a methylene chloride/water mixed solvent having a volume ratio of 1:1 was added thereto. After stirring for 1 h, 20 g of I2 was added in batches. After the addition was completed, the reaction was carried out at room temperature for 3 hours, and the mixture was allowed to stand for stratification. The organic phase was taken and the aqueous phase was extracted with dichloromethane (2 times X 250 mL). The organic phases were combined and used sequentially. Aqueous bisulfite solution, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution were washed twice, dried over anhydrous sodium sulfate, filtered, and spin-dried to give the title compound. Used directly in the next step without purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium iodide; In N,N-dimethyl-formamide; at 120℃; for 12h; | 3) Put 99g Compound II and 400ml DMF into a 1000ml reaction bottle,Add 147g of sodium p-toluenesulfonate, add 1g of potassium iodide, and warm to 120C for 12 hours.The reaction solution was cooled to 60C and poured into 3000ml of water to precipitate a large amount of solids, filtered with suction, and dried at 50 ~ 55C to obtain 115.8g of compound III, with a yield of 80%. |
Tags: 657-84-1 synthesis path| 657-84-1 SDS| 657-84-1 COA| 657-84-1 purity| 657-84-1 application| 657-84-1 NMR| 657-84-1 COA| 657-84-1 structure
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