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CAS No. : | 78146-52-8 | MDL No. : | MFCD00149499 |
Formula : | C8H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YQBLQKZERMAVDO-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 12215922 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
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With sulfuric acid; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
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1.2 g | With acetic acid In ethanol for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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60% | In xylene for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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50% | In xylene for 40h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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66% | In acetic anhydride; acetic acid for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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37% | With triethylamine In tetrahydrofuran Ambient temperature; overnight; |
Yield | Reaction Conditions | Operation in experiment |
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63% | With water In acetone at 35℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
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87% | With scandium tris(trifluoromethanesulfonate) In nitromethane; water for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: benzene / Heating 2: 1) Mg / 1) THF, 2) THF, room temperature, 2h |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: 66 percent / acetic acid; acetic anhydride / 1 h / Heating 2: 82 percent / 25percent aq. NH3 / ethanol / 6 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: 1.) Complex Base 2: 63 percent / CuCl2-CuO, H2O / acetone / 0.5 h / 35 °C |
Yield | Reaction Conditions | Operation in experiment |
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1 g (63%) | With hydrogenchloride; acetic acid In ethanol; ethyl acetate | 42 1-(5-Chloro-2-methoxyphenyl)-5-phenyl-2,4-imidazolidinedione (XIV42) STR52 EXAMPLE 42 1-(5-Chloro-2-methoxyphenyl)-5-phenyl-2,4-imidazolidinedione (XIV42) STR52 N-(5-Chloro-2-methoxyphenyl)urea (1 g, 5 mmol) and phenylglyoxal monohydrate (760 mg, 5 mmol) were taken up in absolute ethanol (100 ml) and acetic acid (1 ml) and 1 ml of conc. HCl added. The reaction mixture was heated at reflux 3.5 h and allowed to stand at 24° C. for 18 h prior to concentration by rotary evaporation. The residue was dissolved in ethyl acetate, washed with sat'd NaHCO3 solution and brine. Recrystallization from methylene chloride/hexanes gave 1 g (63%) mp 200° C.; IR(KBr, ν=cm-1) 3168, 3064, 1772, 1701, 1504, 1444, 1426, 1408, 1260, 1190, 1150; 1 H NMR (300 MHz, CDCl3) δ3.59 (3H, s), 5.60 (1H, s), 6.80 (1H, d, J=8.8 Hz), 7.14-7.37 (7H, m), 8.92 (1H, br.s); MS(DCl)m/z: 317(MH+) Anal. calcd. for C16 H13 ClN2 O3: C, 60.67; H, 4.13; N, 8.84. Found: C, 60.47; H, 4.12; N, 8.80. |
Yield | Reaction Conditions | Operation in experiment |
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In 1,4-dioxane | 7 2-(3,5-Dichlorophenyl)-5-phenyl-2,3-dihydro-1,2,4-triazin-3-one (Compound No. 27) EXAMPLE 7 2-(3,5-Dichlorophenyl)-5-phenyl-2,3-dihydro-1,2,4-triazin-3-one (Compound No. 27) In 50 ml of dioxane was dissolved 2.20 g of 2-(3,5-dichlorophenyl)semicarbazide followed by addition of 1.52 g of phenylglyoxal monohydrate, and the mixture was refluxed for 5 hours. The reaction mixture was then concentrated and the residue was recrystallized from acetonitrile to provide 1.34 g of the title compound. m.p. 160-161° C. NMR [CDCl3 ] δ: 7.38 (t, J=2Hz, 1H), 7.45-7.70 (m, 3H), 7.75 (d, J=2Hz, 2H), 8.05-8.30 (m, 2H), 8.48 (s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
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With sodium tetrahydroborate; trifluoroacetic acid In methanol | 98 1,8-Dihydro-7-[(2-hydroxy-2-phenylethyl)amino]-5-methyl-8-oxo-pyrrolo[4,3,2-de]quinolinium trifluoroacetate EXAMPLE 98 1,8-Dihydro-7-[(2-hydroxy-2-phenylethyl)amino]-5-methyl-8-oxo-pyrrolo[4,3,2-de]quinolinium trifluoroacetate A solution of 10 mg of 7-amino-1-methyl-pyrrolo[4,3,2-de]quinolin-8(1H)-one trifluoroacetate (malaluvamine B) in 1 ml of degassed methyl alcohol is stirred for two hours under nitrogen with rigorous exclusion of oxygen. This mixture is then treated with 4 mg of NaBH4 followed by treatment with 48 mg of phenylglyoxal monohydrate. Chromatography on LH-20 lipophilic sephadex in methyl alcohol/0.1% TFA followed by silica gel flash (15% MeOH/85% CHCl2 /0.1% TFA) gives the desired product. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium tetrahydroborate; trifluoroacetic acid In methanol | 58 1,3,4,8-Tetrahydro-7-[2-hydroxy-2-phenylethyl)amino]-5-methyl-8-oxo-pyrrolo[4,3,2-de]quinolinium trifluoroacetate EXAMPLE 58 1,3,4,8-Tetrahydro-7-[2-hydroxy-2-phenylethyl)amino]-5-methyl-8-oxo-pyrrolo[4,3,2-de]quinolinium trifluoroacetate A solution of 10 mg of 7-amino-1,3,4,8-tetrahydro-5-methyl-8-oxo-pyrrolo[4,3,2-de]quinolinium trifluoroacetate (makaluvamine C) in 1 ml of degassed methyl alcohol is stirred for two hours under nitrogen with rigorous exclusion of oxygen. This mixture is then treated with 4 mg of NaBH4 followed by treatment with 48 mg of phenylglyoxal monohydrate. Chromatography on LH-20 lipophilic sephadex in methyl alcohol/0.1% TFA followed by silica gel flash (15% MeOH/85% CHCl2 /0.1% TFA) gives 13.0 mg of the desired product. 1 H NMR: 13.133(s, 1H, NH-1), 8.763(t, j=6.0 Hz, 1H, NH-9), 7.26-7.46(m, 6H, N(CH2 CH(OH)C6 H5)-9 and CH-2), 5.710(s, 1H, CH-6), 4.935(dd, j=8.5, 5.0 Hz, 2H, N(CH2 CH(OH)C6 H5)-9), 3.903(t, j=7.5 Hz, 2H, CH2 - 4), 3.593(m, 1H, N(CH2 CH(OH)C6 H5)-9), 3.279(s, 3H, N(CH3)-5), 2.922(t, j=7.5 Hz, 2H, CH2 -3). |
Yield | Reaction Conditions | Operation in experiment |
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89% | Pd-on-charcoal; In ethanol; | EXAMPLE XXVIII 3-Phenyl-5-quinoxalinecarboxylic acid STR69 30 g (164.8 mmol) of 2-amino-3-nitrobenzoic acid are suspended in 900 ml of ethanol, 6 g of 5percent strength Pd-on-charcoal are added and hydrogenation is carried out under 3 bar in a Parr apparatus for about 2 hours, until the uptake of hydrogen has ended. The catalyst is filtered off over kieselguhr and 12.8 g (83 mmol) of phenylglyoxal hydrate are added to the solution. The mixture is then stirred at room temperature under nitrogen for 2.5 hours, and the precipitate formed is filtered off with suction, rinsed with ethanol and dried. Yield: 89percent (based on the phenylglyoxal) MS (EI): 250 (M+, 6percent), 206 (M-CO2, 100percent), 103 (12percent), 76 (15percent) |
Yield | Reaction Conditions | Operation in experiment |
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With pyridine | 23 CIS- AND TRANS-2-BENZOYL-5-ACETOXY-1,3-OXATHIOLANE STR39 EXAMPLE 23 CIS- AND TRANS-2-BENZOYL-5-ACETOXY-1,3-OXATHIOLANE STR39 Phenyl glyoxal monohydrate (608 mg, 4.0 mmol) and 2,5-dihydroxy-1,4-dithiane (304 mg, 2.0 mmol) were heated for ca. 5 minutes at 65° C. until the reagents melted. The reaction mixture was diluted with dichloromethane (40 mL). Pyridine (1.32 μL, 16.0 mmol), 4-dimethylamino-pyridine (DMAP) (48 mg), and acetyl chloride (0.85 mL, 12.0 mmol) were added to the stirred solution at 0° C. The reaction mixture was stirred at room temperature for 4.5 hours and diluted with brine solution (15 mL). The organic layer was separated, washed with sodium bicarbonate and brine solutions, dried (sodium sulfate), and evaporated to a brown liquid (1.80 g). The residue was purified by silica gel chromatography eluding with hexanes:EtOAc (3:1) to yield the trans and cis isomers (2.4:1 ratio) (714 mg, 71%); 1 H NMR (CDCl3) δ2.0 (s, 3H), 2.14 (s, 3H), 3.15-3.25 (m, 1H), 3.35-3.45 (m, 1H), 6.42 (s, 1H), 6.51 (s, 1H), 6.7 (m, 1H), 6.9 (m, 1H), 7.4-7.5 (m, 2H), 7.55-7.65 (m, 1H), 7.9-8.0 (m, 2H). | |
With pyridine | 23 CIS- AND TRANS-2-BENZOYL-5-ACETOXY-1,3-OXATHIOLANE STR39 EXAMPLE 23 CIS- AND TRANS-2-BENZOYL-5-ACETOXY-1,3-OXATHIOLANE STR39 Phenyl glyoxal monohydrate (608 mg, 4.0 mmol) and 2,5-dihydroxy-1,4-dithiane (304 mg, 2.0 mmol) were heated for ca. 5 minutes at 65° C. until the reagents melted. The reaction mixture was diluted with dichloromethane (40 mL). Pyridine (1.32 mL, 16.0 mmol), 4-dimethylamino-pyridine (DMAP) (48 mg), and acetyl chloride (0.85 mL, 12.0 mmol) were added to the stirred solution at 0° C. The reaction mixture was stirred at room temperature for 4.5 hours and diluted with brine solution (15 mL). The organic layer was separated, washed with sodium bicarbonate and brine solutions, dried (sodium sulfate), and evaporated to a brown liquid (1.80 g). The residue was purified by silica gel chromatography eluding with hexanes:EtOAc (3:1) to yield the trans and cis isomers (2.4:1 ratio) (714 mg, 71%); 1 H NMR (CDCl3) δ 2.0 (s, 3H), 2.14 (s, 3H), 3.15-3.25 (m, 1H), 3.35-3.45 (m, 1H), 6.42 (s, 1H), 6.51 (s, 1H), 6.7 (m, 1H), 6.9 (m, 1H), 7.4-7.5 (m, 2H), 7.55-7.65 (m, 1H), 7.9-8.0 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol | 5.23 5.23. 5.23. Synthesis Of 2-phenyl-1,4-diaza-anthracene A preferred method of synthesis of 2-phenyl-1,4-diaza-anthracene (Compound 23) is as follows: 20 ml of ethanol containing 0.47 grams of 2,3-diaminonaphthalene and 0.47 grams of phenyl glyoxal hydrate were refluxed for 1.5 hour. Cooling and filtering gave 0.5 g (65%) of a light brown solid with a melting point of 163° C. The product gave the following analytical data: NMR (CDCl3): δ 9.38 (1H, l.c., H2), 8.71, 8.67 (2H, 2d, H5, 10), 8.25, 8.10 (4H, AA'BB'm, H6-9), 7.58 (5H, m, Ph). MS m/e 256 (M+, 100%), 229 (M-CN, 12%), 126 (71%) m/e. | |
In ethanol | 23 5.23. 5.23. Synthesis Of 2-phenyl-1,4-diaza-anthracene A preferred method of synthesis of 2-phenyl-1,4-diaza-anthracene (Compound 23) is as follows: 20 ml of ethanol containing 0.47 grams of 2,3-diaminonaphthalene and 0.47 grams of phenyl glyoxal hydrate were refluxed for 1.5 hour. Cooling and filtering gave 0.5 g (65%) of a light brown solid with a melting point of 163° C. The product gave the following analytical data: NMR (CDCl3): δ 9.38 (1H, l.c., H2), 8.71, 8.67 (2H, 2d, H5,10), 8.25, 8.10 (4H, AA'BB'm, H6-9), 7.58(5H, m, Ph). MS m/e 256 (M+, 100%), 229 (M--CN, 12%), 126(71%) m/e. |
Yield | Reaction Conditions | Operation in experiment |
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45% | 8 Pivaloyloxybromomethyl phenyl ketone EXAMPLE 8 Pivaloyloxybromomethyl phenyl ketone To phenylglyoxal monohydrate {300mg, 1.97mmole) was added pivaloyl bromide (1mL, 9mmole). The reaction mixture was heated at 60°-70° C.for 5hr with stirring. After cooling to room temperature, excess acetyl bromide was removed by concentration. Distillation of the reaction mixtureunder reduced pressure provided 276mg of the desired product as a colorlessoil (45%, 100°-120° C./0.7 torr). 1 H NMR(CDCl3, δ) 8.10-7.10(6H,m), 1.28(9H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 7 Acetoxybromomethyl phenyl ketone EXAMPLE 7 Acetoxybromomethyl phenyl ketone To phenylglyoxal monohydrate (200mg, 1.31mmole) was added acetyl bromide (1mL, 14mmole). The reaction mixture was heated at 65°-70° C. for 2hr with stirring. After cooling to room temperature, excess acetylbromide was removed by concentration. Distillation of the reaction mixture under reduced pressure provided 283mg of the desired product as a colorless oil (79%, 100°-110° C./0.6 torr). 1 H NMR(CDCl3, δ)8.10-7.10(6H,m), 2.16(3H,s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; sodium carbonate In methanol; chloroform; water | 4 Preparation of 2-[4-(3-tert. butylamino-2-hydroxypropoxy)phenyl]-4-phenylimidazole EXAMPLE 4 Preparation of 2-[4-(3-tert. butylamino-2-hydroxypropoxy)phenyl]-4-phenylimidazole A solution of p-(3-tert. butylamino-2-hydroxypropoxy)benzaldehyde (5.0 g., 0.02 mole), phenylglyoxal monohydrate (6.04 g., 0.04 mole), concentrated aqueous ammonia (50 ml.), water (50 ml.) and methanol (200 ml.) is allowed to stand at room temperature for 5 hours. The solution is concentrated to a residual oil under reduced pressure (20 mm. Hg.) and treated with saturated sodium carbonate (50 ml.) and chloroform (3*50 ml.). The organic layer is concentrated to dryness and chromatographed on neutral alumina (500 g.) using a gradient elution technique starting with chloroform. The product is eluted with 10% methanol-90% chloroform. Final purification is accomplished by passing through a column of silica gel (150 g.) and eluted with 20% methanol-80% chloroform. The solvent is removed under reduced pressure (20 mm. Hg.) and the residue crystallized from acetonitrile to give 0.7 g. of 2-[4-(3-tert. butylamino-2-hydroxypropoxy)-phenyl]-4-phenylimidazole, m.p. 176°-178° |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; In benzene; | EXAMPLE 2 In 15 ml of benzene, were dissolved 714 mg of phenylglyoxal monohydrate and 828 mg of (S)-2-(anilinomethyl)pyrrolidine. The resulting solution was refluxed for one hour while removing the formed water by azeotropic distillation. Benzene was removed by distillation in vacuo and the residue was dissolved in 20 ml of ether. To the resulting solution cooled to -70 C., was added dropwise 1.5 equivalents of an ether solution of methylmagnesium iodide. After having been allowed to react for one hour at -70 C., the solution was admixed with 4 ml of saturated aqueous ammonium chloride solution and brought to room temperature. After separating the ether layer, the aqueous layer was neutralized with saturated aqueous sodium hydrogencarbonate solution and then extracted with ether. The ether layer was combined with the previously separated ether layer, admixed with 30 ml of 2% hydrochloric acid and allowed to react for 12 hours at 0 C. The ether layer was separated, washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the ether by distillation in vacuo, the residue was purified by means of a silica gel column chromatography to obtain 471 mg (67%) of (S)-(+)-2-hydroxy-2-phenylpropionaldehyde. [α]D =+244 (C=1.138, benzene); optical yield was 95%. The optical yield was determined by converting the substance into methyl atrolactate methyl ether of known optical rotation. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; sodium hydroxide In methanol; water | 1 5-Phenylpyrazin-2(1H)one EXAMPLE 1 5-Phenylpyrazin-2(1H)one A solution of 2.2 g. (0.02 mol.) of glycinamide hydrochloride (Aldrich Chemical Co.) in 10 ml. of methanol and 4.0 ml. of water was cooled to -40° C. Similarly, 3.0 g. (0.02 mol.) of phenylglyoxal monohydrate (Aldrich Chemical Co.) was dissolved in 14 ml. methanol and cooled to -40° C. The two solutions were mixed and stirred while 3.6 ml. of a 12.5 N sodium hydroxide solution (0.045 mol.) is slowly added at such a rate as to maintain the temperature of the reaction mixture below -10° C. Stirring was continued for 2.0 hr. at -5° C., and then the reaction mixture was stored at 25° C. for 18 hrs. The reaction mixture was cooled to -5° C. and acidified with 2.0 ml. of concentrated hydrochloric acid. The resultant precipitate was isolated by filtration and washed with water, then recrystallized from ethanol to give 1.9 g. of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium borohydrid In methanol; benzene | 9 N-[3-[4-(2-Hydroxyethoxy)phenyl]-1,1-dimethylpropyl]-2-hydroxy-2-phenylethanamine STR31 EXAMPLE 9 N-[3-[4-(2-Hydroxyethoxy)phenyl]-1,1-dimethylpropyl]-2-hydroxy-2-phenylethanamine STR31 A solution of phenyl glyoxal monohydrate (3.6 g) and 3-[4-(2-hydroxyethoxy)phenyl]-1,1-dimethylpropylamine (5 g) in benzene (100 ml) was heated under reflux with removal of water by a Dean and Stark trap. When water removal was complete, the benzene was evaporated under reduced pressure, the residue dissolved in methanol and sodium borohydride (2 g) added. The solution was stirred at ice-water temperature for 15 minutes, the methanol evaporated and the residue portioned between ethyl acetate and water. The organic layer was dried MgSO4 and evaporated to give a solid (6 g) which was purified on a silica gel column eluding with 4% methanol in chloroform. The product (2.8 g) was crystallized from dichloromethane, mp 118°-120° C. τ(DMSO-d6) 8.95 (6H, s), 8.3-8.7 (2H, m), 7.3-7.8 (4H, m), 6.2-6.4 (2H, m), 6.0-6.2 (2H, m), 5.5 (1H, m), 5.2 (3H, bs, replaceable by D2 O), 3.2 (2H, d, J=8 Hz), 2.9 (2H, d, J=8 Hz), 2.6 (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
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18% | In diethyl ether; ethanol; dichloromethane | 1 EXAMPLE 1 EXAMPLE 1 This Example illustrates the preparation of 1,1-diethoxy-2-hydroxy-2-phenyl-3-(1,2,4-triazol-1-yl)propane (compound number 1 of Table I). Phenylglyoxal monohydrate (12.25 g) and 4-toluene-sulphonic acid monohydrate (0.75 g) were dissolved in a mixture of ethanol (30 ml) and 40°-60° petrol (40 ml) and refluxed for 14 hours under a Dean and Stark apparatus. During reflux the lower layer of the azeotrope was removed and the volume of solvent in the reaction vessel was maintained by addition of further ethanol and petrol. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and washed successively with aqueous sodium bicarbonate and water, then dried over magnesium sulphate, and concentrated to give a yellow oil (16.0 g). The crude product was flushed through a column of neutral alumina using dichloromethane/40°-60° petrol (1:1) as solvent to remove traces of the hemiacetal, and gave phenylglyoxal diethyl acetal (13.50 g, 18%) as a pale yellow mobile liquid. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydroxide; sodium hydrogencarbonate In hydrogenchloride; methanol | I EXAMPLE I EXAMPLE I To a mixture of phenylglyoxal hydrate (41.5 g., 0.27 mole) in 250 ml. of methanol at -40° (dry ice-carbon tetrachloride-acetone) is added, with stirring, glycinamide hydrochloride (30.0 g., 0.27 mole) in 250 ml. of methanol, precooled to -40° C. To this stirred mixture 50 ml. of 12.5 N sodium hydroxide is added dropwise while the temperature is maintained at -30° C. The temperature is raised to between -20° and -10° for 1/2 hour, to 0° for 2 hours, and finally to room temperature for 2 hours. The reaction mixture is then cooled in an ice-bath and treated dropwise with 45 ml. of concentrated hydrochloric acid. The pH of the mixture is adjusted to 5 by the portionwise addition of 27 g. of sodium bicarbonate. The mixture is filtered. The solid material is recrystallized from n-butanol. The product is 5-phenylpyrazinol; m.p. 208°-210° |
Yield | Reaction Conditions | Operation in experiment |
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With sodium acetate In ethanol; water | 1 4-Hydroxy-7-Phenylpteridine EXAMPLE 1 4-Hydroxy-7-Phenylpteridine To a hot solution of 4.8 g. of sodium acetate in 30 ml. of water was added 2.25 g. of 4,5-diamino-6-hydroxy pyrimidine sulfate. While stirring, 2.28 g. of phenylglyoxal monohydrate in 10 ml. of hot ethanol was added at once. A precipitate formed immediately. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; hydrogen; sodium acetate;aluminum nickel; In methanol; ethanol; water; | EXAMPLE 2 4-Methoxy-7-Phenylpteridine To a solution of 0.5 g. of metallic sodium in 50 ml. of methanol was added 1.9 g. of <strong>[4316-94-3]4-amino-6-chloro-5-nitropyrimidine</strong>. The reaction mixture was refluxed for 90 minutes and then cooled. The precipitated solid was filtered, washed successively with 50 ml. of water, 30 ml. of methanol and 30 ml. of ether to yield 1.6 g. (86%) of 4-amino-6-methoxy-5-nitropyrimidine. A suspension of 4.8 g. of this compound in 200 ml. of methanol was hydrogenated over 0.5 g. of Raney nickel at room temperature and atmospheric pressure until 2 liters of hydrogen was absorbed. The mixture was filtered and the filtrate evaporated to dryness to yield crude 4,5-diamino-6-methoxypyrimidine which was used without further purification. Of the above, 3.95 g. was dissolved in 80 ml. of water containing 4.8 ml. of concentrated HCl. After adding 13.4 g. of sodium acetate, the solution was heated to 50 degrees C. and a solution of 6.35 g. of phenylglyoxal monohydrate in 30 ml. of ethanol was added. Work-up of the precipitate was carried out as in Example 1 to yield 5.6 g. of crude 4-methoxy-7-phenylpteridine. After two recrystallizations from DMSO, 1.9 g. (28%) of the pure compound was obtained; melting point: 205-7 degrees C. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium acetate; In ethanol; water; | EXAMPLE 1 4-Amino-7-Phenylpteridine To a hot solution of 6.45 g. of sodium acetate in 40 ml. of water was added 3.26 g. of <strong>[49721-45-1]4,5,6-triaminopyrimidine sulfate</strong>. While stirring, 3.04 g. of phenylglyoxal monohydrate in 10 ml. of hot ethanol was added at once. A precipitate formed immediately. |
Yield | Reaction Conditions | Operation in experiment |
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74% | In 1,1-dichloroethane; ethylbenzene | [Example 1] (4'-Ethylbenzoin [3]) [Example 1] (4'-Ethylbenzoin [3]) Phenylglyoxal monohydrate (304 mg, 2mN) and ethylbenzene (0.49ml, 4mM) were dissolved in dichloroethane (4ml), titanium tetrachloride (0.33ml, 3mM) was added, and reacted at room temperature for 2 hours. The reaction mixture was extracted with ethylacetate, the extract was washed with saturated sodium hydrogen carbonate solution and brine, dried with sodium sulfate anhydrous, and then concentrated to obtain a yellow-colored oil. The oil was crystallized from a petroleum ether/diethylether to obtain 357.1 mg (74.0% yield) of 4'-ethylbenzoin. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium borohydrid In methanol; benzene | 13 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1-methylethyl}-2-hydroxy-2-phenylethanamine EXAMPLE 13 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1-methylethyl}-2-hydroxy-2-phenylethanamine A mixture of phenylglyoxal monohydrate (0.86 g) and 2-{4-(2-carbomethoxy-1-methylethenyl)phenyl}-1-methylethanamine (1.4 g) was refluxed in benzene (100 ml) under a Dean and Start head until removal of water was complete (4 h). The solvent was evaporated, methanol (50 ml) added followed by sodium borohydride (0.5 g) and the solution left for 10 min. The methanol was evaporated, the residue shaken with water and extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and evaporated to give an oil which was chromatographed on Kieselgel 60. Elution with 2% methanol-chloroform gave the title compound as a mixture of diastereoisomers m.p. 75°-85° C. (hexane). τ(CDCl3) 8.94 (3H, d, J=6 Hz), 7.45 (3H, d, J=1.5 Hz) 6.9-7.6 (5H, m), 6.25 (3H, s), 4.3 (1H, m), 3.87 (1H, q, J=1.5 Hz), 2.5-3.0 (9H, m). |
Yield | Reaction Conditions | Operation in experiment |
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14 N-{3-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylpropyl}-2-hydroxy-2-phenylethanamine EXAMPLE 14 N-{3-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylpropyl}-2-hydroxy-2-phenylethanamine This was prepared in an identical manner to the compound described in Example 13 using phenylglyoxal monohydrate (1.34 g) and 3-{4-(2-carbomethoxy-1-methylethenyl)phenyl}-1, 1-dimethylpropanamine (2.61 g). The title compound (2.17 g) m.p. 98°-102° C. (benzene-hexane) was obtained after chromatography on Kieselgel 60 eluding with 1% methanolchloroform. τ(CDCl3) 8.85 (6H, s), 8.1-8.7 (2H, m), 6.8-7.8 (9H, m), 6.2 (3H, s), 5.3 (1H, dd), 3.82 (1H broad), 2.65 (9H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)ethyl}-2-hydroxy-2-phenylethanamine EXAMPLE 15 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)ethyl}-2-hydroxy-2-phenylethanamine This was prepared in an identical manner to the compound described in Example 13 using phenylglyoxal monohydrate (1.50 g) and 2-{4-(2-carbomethoxy-1-methylethenyl) phenyl} ethanamine (2.19 g). The title compound (1.18 g) m.p. 120°-125° C. (benzene-hexane) was obtained after chromatography on Kieselgel 60 eluding with 1% methanol-chloroform. τ (CDCl3) 7.5 (3H, d, J=1.5 Hz), 7.5 (2H, m), 7.2 (6H, m), 6.3 (3H, s), 5.29 (1H, dd), 3.87 (1H, q, J=1.5 Hz), 2.85 (2H, d, J=9 Hz), 2.7 (5H, s), 2.6 (2H, d, J=9 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylethyl}-2-hydroxy-2-phenylethanamine EXAMPLE 16 N-{2-(4-{2-Carbomethoxy-1-methylethenyl}phenyl)-1, 1-dimethylethyl}-2-hydroxy-2-phenylethanamine This was prepared in an identical manner to the compound described in Example 13 using phenylglyoxal monohydrate (1.5 g) and 2{4-(2-carbomethoxy-1-methylethenyl)phenyl}-1, 1-dimethylethanamine (2.47 g). The title compound (2.02 g) m.p. 98°-103° C. (benzene/hexane) was obtained after chromatography on Kieselgel 60 eluding with 1% methanolchloroform. τ(CDCl3) 8.9 (6H, s), 7.55 (3H, d, J=1.5 Hz), 7.35 (2H, s), 6.8-7.6 (4H, m) 6.3 (3H, s), 5.4 (1H, dd) 3.85 (1H, q, J=1.5 Hz), 3.0-2.2 (9H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium(IV) oxide In 1,4-dioxane | 1.A.B Step B Step B 4-Fluorophenylglyoxal Hydrate The title compound was prepared using essentially the same procedure as described by H. A. Riley and A. R. Gray in Organic Synthesis, Collective Volume II, p. 509 for the preparation of phenylglyoxal hydrate, but using 4'-fluoroacetophenone in place of acetophenone. Thus, 18.5 g of selenium dioxide was dissolved in 100 mL of dioxane by warming to 50° C. and stirring until all was in solution. To this solution was added 23 g of 4'-fluoroacetophenone and the reaction was refluxed for 4 h. The hot solution was decanted from the solid selenium and the dioxane and water were removed by distillation through a short column at atmospheric pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: phthalimide; phenylglyoxal monohydrate; methyl vinyl ketone With triphenylphosphine In tetrahydrofuran at 27 - 30℃; for 4.5h; Inert atmosphere; Stage #2: With dmap; acetic anhydride; triethylamine In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With 2-chloroanthracene-9,10-dione; oxygen In ethyl acetate for 10h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With PVPP*OTf In water at 20℃; for 1h; | 2.2 Typical experimental procedure General procedure: A mixture of 1,2-dicarbonyl compounds (1 mmol), aryl 1,2-diamines (1 mmol) dissolved in 4 mL water, and PVPP·OTf (30 mg) was stirred for 1 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated and purified by recrystallization from hot ethanol to afford pure products. Products were characterized by comparison of their physical and spectral data with those of authentic samples. Spectroscopic data for selected examples as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With PVPP*OTf In water at 20℃; for 1h; | 2.2 Typical experimental procedure General procedure: A mixture of 1,2-dicarbonyl compounds (1 mmol), aryl 1,2-diamines (1 mmol) dissolved in 4 mL water, and PVPP·OTf (30 mg) was stirred for 1 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated and purified by recrystallization from hot ethanol to afford pure products. Products were characterized by comparison of their physical and spectral data with those of authentic samples. Spectroscopic data for selected examples as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With sodium sulfate; triethylamine In toluene for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium sulfate; triethylamine / toluene / 6 h / Reflux 2: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid / chloroform / 72 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77 % ee | With C32H29N3O3S In water at 25℃; enantioselective reaction; | 2.3 General procedure for the aldehyde-aldehyde aldol reaction using phenylglyoxal monohydrate: General procedure: To a mixture of the phenylglyoxal monohydrate (0.25 mmol, 0.028 g) and catalyst (10 mol%) at the indicated temperature was added the corresponding aldehyde (0.5 mmol). The reaction was stirred until the phenylglyoxal was consumed (monitored by TLC). Wittig Reagent (0.178 g, 0.5mmol) was added and reaction mixture was stirred for 2 h. Upon completion, the Witting reaction was quenched by passing through silica gel pad, and concentrated in vacuo. The resulting residue was purified by chromatography (hexanes/AcOEt) to yield the unsaturated ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 % ee | With C32H29N3O3S In water at 25℃; enantioselective reaction; | 2.3 General procedure for the aldehyde-aldehyde aldol reaction using phenylglyoxal monohydrate: General procedure: To a mixture of the phenylglyoxal monohydrate (0.25 mmol, 0.028 g) and catalyst (10 mol%) at the indicated temperature was added the corresponding aldehyde (0.5 mmol). The reaction was stirred until the phenylglyoxal was consumed (monitored by TLC). Wittig Reagent (0.178 g, 0.5mmol) was added and reaction mixture was stirred for 2 h. Upon completion, the Witting reaction was quenched by passing through silica gel pad, and concentrated in vacuo. The resulting residue was purified by chromatography (hexanes/AcOEt) to yield the unsaturated ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In ethanol for 10h; Reflux; | 3-(5,6-Diphenylpyridine-2-yl)-5-phenyl-1,2,4-triazine (7b). Amidrazone 6 (285 mg, 0.99 mmol) was added to a solution of phenylglyoxal hydrate (150 mg, 0.99 mmol) in ethanol (80 mL) and the mixture obtained was refluxed for 10 h. The solvent was evaporated at reduced pressure, the residue was recrystallized from ethanol. The yield was 155 mg (0.40 mmol, 40%), m.p. 142-144 °C. Found (%): C, 80.74; H, 4.53; N, 14.61. C26H18N4. Calculated (%): C, 80.81; H, 4.69; N, 14.50. 1H NMR (DMSO-d6),: 7.25-7.35 (m, 8 H, Ph); 7.43-7.47 (m, 2 H, Ph); 7.60-7.68 (m, 3 H, Ph (triazine)); 8.04 (d, 1 H, pyridine, J = 8.1 Hz); 8.45-8.49 (m, 2 H, Ph (triazine)); 8.58 (d, 1 H, pyridine, J = 8.1 Hz); 10.09 (s, 1 H, H(6)). MS (ESI), m/z (%): 387.16 [M + H]+ (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With caesium carbonate; toluene-4-sulfonic acid hydrazide In chloroform at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid hydrazide; caesium carbonate / chloroform / 0.5 h / 20 °C 2: iron(III) trifluoromethanesulfonate / water / 6 h / 70 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid hydrazide; caesium carbonate / chloroform / 0.5 h / 20 °C 2: iron(III) trifluoromethanesulfonate / water / 6 h / 70 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid hydrazide; caesium carbonate / chloroform / 0.5 h / 20 °C 2: iron(III) trifluoromethanesulfonate / water / 6 h / 70 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With tropylium tetrafluoroborate In acetonitrile at 70℃; for 5h; Inert atmosphere; Green chemistry; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: ethyl acetoacetate; 4-amino-o-xylene In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 7h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: ethyl acetoacetate; <i>p</i>-toluidine In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 7h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: ethyl acetoacetate; 4-chloro-aniline In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 7h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: ethyl acetoacetate; 4-methoxy-aniline In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 7h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: ethyl acetoacetate; aniline In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: ethyl acetoacetate; para-methylbenzylamine In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: <i>p</i>-toluidine; acetoacetic acid methyl ester In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 4-chloro-aniline; acetoacetic acid methyl ester In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 4-methoxy-aniline; acetoacetic acid methyl ester In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: 4-amino-o-xylene; acetylacetone In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 10h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: <i>p</i>-toluidine; acetylacetone In ethanol at 20℃; for 1h; Stage #2: 1,3-dimethylbarbituric acid; phenylglyoxal monohydrate In ethanol for 10h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.5% | Stage #1: (trifluoromethyl)trimethylsilane; phenylglyoxal monohydrate In 1,2-dimethoxyethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With cesium fluoride In 1,2-dimethoxyethane at 0℃; for 1.66667h; | 9 Example 9. Preparation of SM-9: 2-hydroxy-2-trifluoromethylacetophenone A 500 ml flask was charged with phenylglyoxal hydrate (15.21 g, 100 mmol, 1.0 eq.), (trifluoromethyl)trimethylsilane (31.1 g, 205 mmol, 2.05 eq.), and dimethoxyethane (200 mL) under nitrogen stream. The mixture was stirred for 10 minutes at 0° C., after which CsF (280 mg, 2.0 mmol, 0.02 eq.) was added to the mixture in small portions over 10 minutes. The reaction mixture was stirred for 1.5 hours at 0° C. (caution: this reaction has an induction period and is exothermic). Subsequently, the mixture was stirred for 30 minutes at room temperature. THF (20 mL) and 6N HCl (80 mL) were added followed by stirring for 1.5 hours. The upper layer was separated, the lower layer was extracted with Et2O (100 ml*2), and the organic layers were combined. The organic solution was washed with brine (50 mL), dried over anhydrous MgSO4, and filtered. Solvents were removed in an evaporator and the crude product was purified by column chromatography (hexane/AcOEt) to obtain the target compound as a white solid (2.96 g, 14.5% yield). 1H-NMR (CDCl3), delta (ppm): 4.28 (d, J=8.3 Hz, 1H), 5.44 (qd, J=6.6, 8.3 Hz, 1H), 7.58 (dd, J=7.8, 7.9 Hz, 1H), 7.73 (t, J=7.5 Hz, 1H), 8.01 (d, J=7.7 Hz, 1H), 19F-NMR (CDCl3, standard: C6F6=-162.2 ppm), delta (ppm): -74.34 (d, J=6.6 Hz, 3F). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1,2-dimethoxyethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 1.67 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.92 h / -40 °C / Inert atmosphere 2.2: 3.17 h / -40 - 10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1,2-dimethoxyethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 1.67 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -30 - -20 °C / Inert atmosphere 2.2: 2.58 h / -20 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With acetic acid In ethanol; water at 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With air In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 6h; | 1.2 Step 2: 2-(2-pentyl)imidazo[1,2-a]pyridine (0.20 mmol) synthesized in the first step,Phenylglyoxal hydrate (0.24 mmol)And xylene (2 mL) was added to the reaction flask to react; in the presence of air, stirring at 80 ° C for 6 hours;After the reaction was completed, the reaction system was cooled to room temperature.Extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentratedPurification by silica gel column chromatography (4:1 petroleum ether to ethyl acetate) to give the product 1-(2-pentylimidazo[1,2-a]Pyridin-3-yl)-2-phenylethane-1,2-dione. The reaction yield was 52%, and its structural formula was as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With air In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 6h; | 2.2 Step 2: 2-(2-(cyclopropane)imidazo[1,2-a]pyridine (0.20 mmol) synthesized in the first step,Phenylglyoxal hydrate (0.24 mmol) and xylene (2 mL) were added to the reaction flask to react; in the presence of air, the mixture was stirred at 80 ° C for 6 hours; after the reaction was completed, the reaction system was cooled to room temperature. Extracted with ethyl acetate,After drying over anhydrous sodium sulfate, it was purified by concentrated silica gel column chromatography (yield of petroleum ether and ethyl acetate: 4:1).To obtain the product 1-(2-cyclopropylimidazo[1,2-a]pyridin-3-yl)-2-phenylethane-1,2-dione.The reaction yield was 56%, and its structural formula was as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. Analytical Data of Product 3 Product 3aa: Yellow oil, Yield 92%; 1H NMR (400 MHz, CDCl3) δ 8.09 (dt, J = 8.5, 1.5 Hz, 2H), 7.70 - 7.62 (m, 3H), 7.55 - 7.48 (m, 3H), 7.43 - 7.38 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 187.41, 179.40, 177.51, 171.70, 133.89, 132.97, 132.62, 131.27, 130.67, 130.54, 129.91, 129.47, 128.73, 127.91, 127.72, 125.27, 118.13, 103.81, 98.13, 93.46, 86.02, 83.96; HRMS (TOF) m/z [M + Na]+ Calcd for C16H10O2 257.0573 found 257.0590. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With oxygen; copper diacetate; acetic acid In toluene at 80℃; for 4h; Sealed tube; | Experimental Procedures General procedure: Arylglyoxals 1 (0.2 mmol), alkynes 2 (0.2 mmol), Cu(OAc)2 (10 mol%) and AcOH (20 mol%) were dissolved in 4 mL toluene and stirred at 80 °C for 4h in a sealed tube equipped with an O2 balloon. Monitored by TLC, when the reaction was completed, the reaction mixture was cooled to room temperature, then quenched with saturated NH4Cl solution and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4 and directly subjected to silica gel column chromatography (hexane/dichloromethane=1:1) to afford SI-4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (S)-2-((2-(hydroxydi-p-tolylmethyl)pyrrolidin-1-yl)methyl)-6-(trifluoromethyl)phenol; copper(II) bis(trifluoromethanesulfonate); triethylamine In acetone at 0 - 5℃; for 2.5h; | 7 Copper-chiral ligand L2 complex catalyzed the Mukaiyama aldol reaction of phenylglyoxal monohydrate to prepare 1,4-diphenyl-2-hydroxy-1,4-dibutanone compound S-3aa Add 1mL of acetone to the 10mL reaction tube,Add copper trifluoromethanesulfonate (7.22mg, 0.02mmol),Stir for one hour to fully dissolve the copper salt;Add the chiral ligand L2 (4.2 mg, 0.1 mmol) and triethylamine (2.8 μL, 0.02 mmol) prepared in Example 1 above,The reaction was transferred to 0°C and stirred for one hour to obtain a chiral copper complex.Add phenylglyoxal monohydrate 1a (phenylglyoxal monohydrate) (15.2mg, 0.1mmol) and the enol silyl ether 2a (42μL, 0.2mmol) shown in the above formula 3 into the system,The reaction system was transferred to 5°C and reacted for 2.5 hours.After the end of the reaction was monitored by thin layer chromatography, it was extracted with ethyl acetate,Reverse extraction with saturated brine, dry with anhydrous sodium sulfate,After concentration under reduced pressure, the residue is separated by column chromatography,Use petroleum ether/ethyl acetate to wash with a gradient of 20/1 to 5/1,A white solid product S-3aa (89% yield, 94% ee) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With (S)-2-((2-(hydroxydi-p-tolylmethyl)pyrrolidin-1-yl)methyl)-6-(trifluoromethyl)phenol; copper(II) bis(trifluoromethanesulfonate); triethylamine In acetone at 0 - 5℃; for 2.5h; | 22 Copper-chiral ligand L2 complex catalyzes the Mukaiyama aldol reaction of furan-derived silyl enol ether to prepare 1,4-diphenyl-2-hydroxy-1,4-dibutanone compound S-3ab Add 1mL of acetone to the 10mL reaction tube,Add copper trifluoromethanesulfonate (7.22mg, 0.02mmol),Stir for one hour to fully dissolve the copper salt;Add the chiral ligand (4.2 mg, 0.1 mmol) and triethylamine (2.8 μL, 0.02 mmol) prepared in Example 1 above,The reaction was transferred to 0°C and stirred for one hour to obtain a chiral copper complex.Add phenylglyoxal monohydrate 1a (2-(furan-2-yl)-2-oxoacetaldehyde) (15.2mg, 0.1mmol) and the furan-derived silicon enol shown in formula 4 above into the system Ether 2b (42μL, 0.2mmol),The reaction system was transferred to 5°C and reacted for 2.5 hours.After the end of the reaction was monitored by thin layer chromatography, it was extracted with ethyl acetate,Reverse extraction with saturated brine, dry with anhydrous sodium sulfate,After concentration under reduced pressure, the residue is separated by column chromatography,Use petroleum ether/ethyl acetate to wash with a gradient of 20/1 to 5/1,A white solid product S-3ab (89% yield, 94% ee) was obtained. |
Tags: 78146-52-8 synthesis path| 78146-52-8 SDS| 78146-52-8 COA| 78146-52-8 purity| 78146-52-8 application| 78146-52-8 NMR| 78146-52-8 COA| 78146-52-8 structure
[ 1171381-90-0 ]
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