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Product Details of [ 6656-60-6 ]

CAS No. :6656-60-6 MDL No. :MFCD01660185
Formula : C10H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :JJANSRGIKCRCFG-UHFFFAOYSA-N
M.W :178.18 Pubchem ID :23137
Synonyms :

Safety of [ 6656-60-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6656-60-6 ]

* 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.

  • Downstream synthetic route of [ 6656-60-6 ]

[ 6656-60-6 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 6656-60-6 ]
  • [ 141396-05-6 ]
YieldReaction ConditionsOperation in experiment
92% With glucose dehydrogenase; ketoreductase; NADPH In dimethyl sulfoxide at 34℃; for 13h;
90% With D-glucose; immobilized baker's yeast In water at 35℃; for 72h;
With baker's yeast In water at 35℃; for 72h; reduction of other 2-oxoalkyl benzoates;
With fermenting yeast
With D-glucose 6-phosphate; MES buffer pH 6.0 at 35℃; for 12h; α-acetoxy ketone reductase from bakers' yeast, glucose 6-phosphate dehydrogenase, NADPH;

  • 3
  • [ 78-95-5 ]
  • [ 65-85-0 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; potassium iodide In tetrahydrofuran at 20 - 40℃; for 16h; 1.1; 2.1 1) Preparation of 2-oxopropyl benzoate A mixture of 100g of benzoic acid, 79.5g of chloroacetone and 500ml of tetrahydrofuran was stirred at room temperature, and the temperature was controlled below 40°C. 226g of potassium carbonate and 1g of potassium iodide catalyst were added to the lower reaction mixture, and the resulting mixture was stirred at 40°C for 16 hours . The reaction mixture was cooled in an ice bath, and then 200 ml of purified water was added dropwise to the reaction mixture. Separate the water phase, and then wash with 10% sodium chloride aqueous solution. After washing, the organic phase is concentrated to no distillate, and then 500ml n-heptane is added to cool down at 5°C to crystallize for 0.5 hours, and then the turbid system is filtered. The obtained solid was washed with n-heptane and dried under reduced pressure to obtain 138.4 g of the target compound with a molar yield of 95% and a purity of 99.5%.
70% With triethylamine In acetone for 24h; Ambient temperature;
bei der Einwirkung auf Kaliumbenzoat;
  • 4
  • [ 532-32-1 ]
  • [ 78-95-5 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
With sodium iodide In acetone
With tetrabutylammomium bromide In benzene for 3h; Heating;
With IRA-400 1.) H2O, 2.) EtOH, room temperature, 4 h.; Yield given. Multistep reaction;
In N,N-dimethyl-formamide at 100℃; for 21h;
In N,N-dimethyl-formamide at 100℃; for 21h;
In N,N-dimethyl-formamide at 100℃; for 21h;

  • 5
  • diethyl(prop-2-yn-1-yl)sulfonium bromide [ No CAS ]
  • [ 65-85-0 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol for 648h;
  • 6
  • [ 6750-04-5 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
81% With p-toluenesulfonic acid monohydrate; acetic acid In 1,2-dichloro-ethane at 100℃; for 18h; Sealed tube; General procedures for alkyne hydration General procedure: The corresponding alkyne (1 mmol) was added to a solution of p-toluenesulfonic acidmonohydrate (1 mmol, 0.190 g), acetic acid (0.5 mL) in CH2Cl2 (1.0 mL). Thereaction was then sealed and stirred at the indicated temperature (oC) and for theindicated amount of times (h) in Table 2. After completion, saturated aqueousNaHCO3 (10 mL) was added to quench the reaction and then extracted with CH2Cl2(10 mL×3). The organic layer was dried over Na2SO4 and concentrated in vacuo. Theresidue was purified by column chromatography to give the pure product. Forsubstrates 1j. 1l, 1n, 1p and 1q, DCE was used as solvent in consideration ofoperation convenience.
67% With diethyl ether; boron trifluoride; trifluoroacetic acid; mercury(II) oxide In methanol at 60℃; for 4h;
  • 7
  • [ 107-19-7 ]
  • [ 65-85-0 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
99% With dichlororuthenium(II) (p-cymene)(1,3,5-triaza-7-phosphaadamantane)
92% With (η6-p-MeC6H4CHMe2)Cl2Ru(PMe3) In toluene at 60℃; for 6h;
92% With C44H40O8P2Ru; sodium carbonate In toluene at 90℃; for 24h;
77% With cis-[Ru(κ2-O2CMe)2(PPh3)2] In toluene at 120℃; for 16h; Inert atmosphere;
67% With {RuCl2(p-cymene)[(R)-BINOL-N,N-dibenzylphosphoramidite] In cyclohexane at 90℃; for 5h;
67% With trans-[RuCl2(η3:η3-2,7-dimethylocta-2,6-diene-1,8-diyl)(PPh3)] In water at 60℃; for 24h; Sealed tube; Inert atmosphere;
60% With RuCl2(η-C6H6)(TPPMS) In water at 100℃; for 3h; Inert atmosphere;
With C70H72Cl6FeP3Ru3 In chlorobenzene at 80℃; for 1h; Inert atmosphere;
With [RuCl26-p-cymene)(P(2-(5-Me)C4H2O)2Fc)] In chlorobenzene at 80℃; for 9h; Inert atmosphere; Schlenk technique; General procedure for the catalytic reactions Benzoic acid (366 mg, 3.0 mmol, 1.0 equiv), acenaphthene (116 mg, 750 μmol, 0.25 equiv, internal standard) and the respective catalyst (9, 10 or 11, 1.0 mol-% based on Ru) were dissolved in chlorobenzene (15 mL). After addition of propargyl alcohol (252 mg, 4.5 mmol, 1.5 equiv) the reaction mixture was stirred at 80 °C and samples (0.5 mL) were taken in different intervals (30-90 min). The samples were dried in vacuum and the conversions were determined by 1H NMR spectroscopy.
99 %Spectr. With Ru(CO)2(P[p-C6H4-CF3]3)2(O2CPh)2; acenaphthene In toluene at 80℃; for 5h;
90 %Spectr. With sodium carbonate In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction; 4.2 Catalytic runs General procedure: In a typical run, the acid (0.78mmol), propargyl alcohol (0.07ml, 1.2mmol), Na2CO3 (4mg, 0.03mmol) and the catalyst (1.4mol %), were dissolved in toluene (10ml) and stirred for 12hat 100°C. After cooling to room temperature, the mixture was filtered and the filtrate was then evaporated under a vacuum. The residue was then purified by thin layer chromatography to afford the product.

Reference: [1]Musengimana, Eric; Fatakanwa, Claver [Journal of the Iranian Chemical Society, 2016, vol. 13, # 2, p. 253 - 259]
[2]Devanne, Dominique; Ruppin, Christophe; Dixneuf, Pierre H. [Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 925 - 926]
[3]Jeschke, Janine; Gäbler, Christian; Korb, Marcus; Rüffer, Tobias; Lang, Heinrich [European Journal of Inorganic Chemistry, 2015, vol. 2015, # 18, p. 2939 - 2947]
[4]Location in patent: experimental part Hiett, Nicholas P.; Lynam, Jason M.; Welby, Christine E.; Whitwood, Adrian C. [Journal of Organometallic Chemistry, 2011, vol. 696, # 1, p. 378 - 387]
[5]Costin, Stephen; Rath, Nigam P.; Bauer, Eike B. [Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2414 - 2424]
[6]Location in patent: experimental part Cadierno, Victorio; Francos, Javier; Gimeno, Jose [Organometallics, 2011, vol. 30, # 4, p. 852 - 862]
[7]Location in patent: experimental part Cadierno, Victorio; Francos, Javier; Gimeno, Jose [Green Chemistry, 2010, vol. 12, # 1, p. 135 - 143]
[8]Location in patent: experimental part Milde, Bianca; Rueffer, Tobias; Lang, Heinrich [Inorganica Chimica Acta, 2012, vol. 387, p. 338 - 345]
[9]Schreiner, Claus; Jeschke, Janine; Milde, Bianca; Schaarschmidt, Dieter; Lang, Heinrich [Journal of Organometallic Chemistry, 2015, vol. 785, p. 32 - 43]
[10]Jeschke, Janine; Korb, Marcus; Rüffer, Tobias; Gäbler, Christian; Lang, Heinrich [Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 4069 - 4081]
[11]Barik, Chandan Kr; Tessensohn, Malcolm E.; Webster, Richard D.; Leong, Weng Kee [Journal of Organometallic Chemistry, 2019, vol. 889, p. 40 - 44]
  • 8
  • [ 108164-55-2 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
With methoxytriphenylmethane; sodium hydrogencarbonate 1.) CH2Cl2, 0 deg C, 1.5 h; Yield given. Multistep reaction;
  • 9
  • [ 6656-60-6 ]
  • [ 89686-16-8 ]
  • 2-<(Benzoyloxy)methyl>-2,5-dihydro-1-hydroxy-2,4,5,5-tetramethylimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With ammonium acetate In methanol 1.) 5 min, 2.) r.t., 1 h;
  • 10
  • [ 98-88-4 ]
  • [ 116-09-6 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
99% With dmap; triethylamine In dichloromethane at 25℃; for 1h;
87.8% With pyridine In tetrahydrofuran at 0 - 20℃; for 43h; 5.a (5a) 2-oxopropyl benzoate To a pyridine (25 ml) and THF (10 ml) solution of hydroxyacetone (5 g, 67.5 mmol), benzoyl chloride (12 ml, 103 mmol) was added dropwise at 0° C. in a nitrogen atmosphere and the mixture was stirred for 43 hours at room temperature. Ice was added to the reaction mixture, which was then diluted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient). Desired fractions were concentrated to obtain the title compound (10.56 g, 87.8% yield) as a light yellow oil. 1H NMR(400 MHz, DMSO-d6) δppm; 2.14(3H, s), 5.01(2H, s), 7.51-7.58(2H, m), 7.65-7.70(1H, m), 7.95-8.00(2H, m).
76.5% With pyridine for 12h; Ambient temperature;
8 g With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1.25h; 14.1 Step 1 (ME-S1) Step 1 (ME-Si):Triethyamine (18.5 mL, 135 mmol) was added to a solution of hydroxyacetone (5.0 g, 67.49mmol) in dichloromethane (80 mL) at 0°C. Benzoyl chloride (7.84 mL, 67.49 mmol) wasadded drop wise over 15 mm and DMAP (200 mg) was added. The reaction mass was warmed to room temperature and stirred for 1 h. The reaction was quenched with water and extracted with dichloromethane. The combined organic layer was washed successively with water, brine; dried over anhydrous sodium sulfate and concentrated in vacuum to afford thecrude intermediate. Purification by column chromatography over silica gel (60-1 20mesh) and using 8% ethyl acetate in pet ether as the eluent afforded 8 g of ME-Si as a colorless liquid.

  • 11
  • [ 6656-60-6 ]
  • [ 96-24-2 ]
  • [ 187996-09-4 ]
YieldReaction ConditionsOperation in experiment
72.4% With toluene-4-sulfonic acid In toluene for 48h; Heating;
  • 12
  • [ 6656-60-6 ]
  • [ 60-24-2 ]
  • [ 207556-16-9 ]
YieldReaction ConditionsOperation in experiment
65% With toluene-4-sulfonic acid In toluene for 18h; Heating;
  • 13
  • [ 6656-60-6 ]
  • [ 143-33-9 ]
  • Benzoic acid 2-cyano-2-hydroxy-2-methyl-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydrogencarbonate In diethyl ether; water for 48h; Ambient temperature;
  • 14
  • [ 6656-60-6 ]
  • [ 100-52-7 ]
  • 4-hydroxy-2-oxo-4-phenylbutyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With chloro-trimethyl-silane; tributyl-amine; titanium tetrachloride In dichloromethane at -78℃; for 3h;
86% Stage #1: 2-oxopropyl benzoate With chloro-trimethyl-silane; tributyl-amine; titanium tetrachloride In dichloromethane at -78℃; for 0.5h; Stage #2: benzaldehyde In dichloromethane at -78℃;
  • 15
  • [ 27607-77-8 ]
  • [ 6656-60-6 ]
  • Benzoic acid (E)-2-trimethylsilanyloxy-propenyl ester [ No CAS ]
  • benzoic acid 2-trimethylsilanyloxy-allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,6-dimethylpyridine In benzene at 0℃; for 3h; Title compound not separated from byproducts;
  • 16
  • [ 6656-60-6 ]
  • [ 284035-47-8 ]
  • Benzoic acid (4R,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
  • Benzoic acid (4S,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (-)-diisopinocamphenylborane chloride In diethyl ether at -78℃; for 3h; Title compound not separated from byproducts;
With di-n-butylboryl trifluoromethanesulfonate; triethylamine In dichloromethane at -78 - 0℃; for 3h; Title compound not separated from byproducts;
  • 17
  • [ 6656-60-6 ]
  • [ 284035-47-8 ]
  • Benzoic acid (4R,5S,6R)-10-benzyloxy-4,6-dihydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
  • Benzoic acid (4S,5S,6R)-10-benzyloxy-4,6-dihydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-oxopropyl benzoate; (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal With di-n-butylboryl trifluoromethanesulfonate In dichloromethane at -78 - 0℃; for 3h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; Title compound not separated from byproducts;
  • 18
  • [ 67-56-1 ]
  • [ 6656-60-6 ]
  • [ 284035-47-8 ]
  • [ 284035-51-4 ]
  • Benzoic acid (2R,4R,5R,6R)-6-(4-benzyloxy-butyl)-4-hydroxy-2-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 12% Stage #1: 2-oxopropyl benzoate; (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal With di-n-butylboryl trifluoromethanesulfonate In dichloromethane at -78 - 0℃; for 3h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; Stage #3: methanol With camphor-10-sulfonic acid at 20℃; for 1h;
  • 19
  • [ 27607-77-8 ]
  • [ 6656-60-6 ]
  • [ 284035-47-8 ]
  • Benzoic acid (2R,3R,4R)-1-acetyl-8-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-octyl ester [ No CAS ]
  • Benzoic acid (4R,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
  • Benzoic acid (4S,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: trimethylsilyl trifluoromethanesulfonate; 2-oxopropyl benzoate With 2,6-dimethylpyridine In benzene at 0℃; for 3h; Stage #2: (2S,3R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptanal With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 3h;
  • 20
  • [ 2568-25-4 ]
  • [ 6656-60-6 ]
  • [ 51591-52-7 ]
  • [ 37086-84-3 ]
  • 21
  • [ 6656-60-6 ]
  • [ 103548-13-6 ]
YieldReaction ConditionsOperation in experiment
91% With glucose dehydrogenase; ketoreductase; NADPH In dimethyl sulfoxide at 34℃; for 4h;
  • 22
  • [ 6656-60-6 ]
  • [ 784193-14-2 ]
YieldReaction ConditionsOperation in experiment
94% With diethylamino-sulfur trifluoride In ethanol; dichloromethane
4 g With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 18h; 14.2 Step 2 (ME-S2) Step 2 (ME-52):Diethylamino sulfurtrifluoride (5.9 mL, 44.94 mmol) was added to a solution of ME-Si (4.0 g,22.47 mmol) in dichloromethane (40 mL) at 0°C and the solution was stirred at roomtemperature for 18 h. The reaction was quenched with ice water and the mixture was extracted with dichloromethane. The combined organic layer was washed successively with water, brine; dried over anhydrous sodium sulfate and concentrated in vacuum to afford 4.Og of ME-52 as a brown liquid.
  • 23
  • [ 6656-60-6 ]
  • [ 104-94-9 ]
  • (+)-N-(4-methoxyphenyl)-(1-methyl-2-benzoate-ethyl)amine [ No CAS ]
  • (-)-N-(4-methoxyphenyl)-(1-methyl-2-benzoate-ethyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 5A molecular sieve; ethyl Hantzsch ester In benzene at 40℃; for 96h; Title compound not separated from byproducts;
  • 24
  • [ 201230-82-2 ]
  • oxiran-2-ylmethyl benzoate [ No CAS ]
  • 4-(benzoyloxymethyl)-2-propiolactone [ No CAS ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
With [(salph)Cr(THF)2][Co(CO)4] In 1,2-dimethoxyethane at 22℃; for 6h;
  • 25
  • [ 6656-60-6 ]
  • Benzoic acid (4R,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-lutinine / benzene / 3 h / 0 °C 2: BF3*Et2O / CH2Cl2 / 3 h / -78 °C
  • 26
  • [ 6656-60-6 ]
  • Benzoic acid (4S,5R,6R)-10-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-2-oxo-decyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,6-lutinine / benzene / 3 h / 0 °C 2: BF3*Et2O / CH2Cl2 / 3 h / -78 °C
  • 27
  • [ 6656-60-6 ]
  • 2-benzoyloxymethyl-2-methanesulfonyloxypropionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / NaHCO3 / diethyl ether; H2O / 48 h / Ambient temperature 2: 0.95 g / Et3N / CH2Cl2 / 21 h / Ambient temperature
  • 28
  • [ 6656-60-6 ]
  • 4-amino-5-benzoyloxymethyl-5-methyl-1,2-oxathiole 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 78 percent / NaHCO3 / diethyl ether; H2O / 48 h / Ambient temperature 2: 0.95 g / Et3N / CH2Cl2 / 21 h / Ambient temperature 3: 54 percent / DBU / acetonitrile / 24 h / Ambient temperature
  • 29
  • [ 6656-60-6 ]
  • [ 207556-17-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / pTSA / toluene / 18 h / Heating 2: 75 percent / benzene / 4 h / Heating
  • 30
  • [ 6656-60-6 ]
  • Benzoic acid (2R,4S)-4-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-methyl-[1,3]oxathiolan-2-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / pTSA / toluene / 18 h / Heating 2: 75 percent / benzene / 4 h / Heating 3: TMSI / CH2Cl2
  • 31
  • [ 6656-60-6 ]
  • Benzoic acid (2S,4S)-4-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-methyl-[1,3]oxathiolan-2-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / pTSA / toluene / 18 h / Heating 2: 75 percent / benzene / 4 h / Heating 3: TMSI / CH2Cl2
  • 32
  • [ 6656-60-6 ]
  • 2-<(Benzoyloxy)methyl>-2,5-dihydro-2,4,5,5-tetramethylimidazole-1-oxyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 10 percent / NH4OAc / methanol / 1.) 5 min, 2.) r.t., 1 h 2: 94 percent / PbO2 / diethyl ether / 2 h / Ambient temperature
  • 33
  • [ 98-88-4 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / NEt3 / benzene / 3 h / Heating 2: 95 percent / NEt3 / ((C6H5)3)2Pd(II)-chloride, CuI / 3 h / Ambient temperature 3: 67 percent / HgO, BF3/EtOEt, trifluoroacetic acid / methanol / 4 h / 60 °C
  • 34
  • [ 116228-38-7 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / NEt3 / ((C6H5)3)2Pd(II)-chloride, CuI / 3 h / Ambient temperature 2: 67 percent / HgO, BF3/EtOEt, trifluoroacetic acid / methanol / 4 h / 60 °C
  • 35
  • [ 540726-99-6 ]
  • [ 6656-60-6 ]
  • [ 913695-99-5 ]
YieldReaction ConditionsOperation in experiment
29.1% With toluene-4-sulfonic acid; orthoformic acid triethyl ester In ethyl acetate at 20℃; for 13.5h; 5.b (5b) (8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methyl benzoate The 2-oxopropyl benzoate (4 g, 22.4 mmol) obtained in the step (5a) was mixed with 1,3-dioxolan-2,2-diyldimethanol (3 g, 22.4 mmol) obtained in the step (4c), triethyl orthoformate (3.8 ml, 22.8 mmol), and p-toluenesulfonic acid monohydrate (200 mg, 1.05 mmol). The mixture was stirred at room temperature for 13.5 hours. To the mixture, a saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added. The organic layer was washed with water twice and with a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient) and desired fractions were concentrated to obtain the title compound (1.92 g, 29.1% yield) as a colorless oil. 1H NMR(400 MHz, DMSO-d6) δppm; 1.41(3H, s), 3.64-3.76(4H, m), 3.80-3.88(4H, m), 4.33(2H, s), 7.50-7.57(2H, m), 7.64-7.70(1H, m), 7.92-8.00(2H, m).
  • 36
  • [ 583-04-0 ]
  • [ 6656-60-6 ]
YieldReaction ConditionsOperation in experiment
81% With dichloro bis(acetonitrile) palladium(II); bismuth vanadate; water In N,N-dimethyl-formamide at 120℃; Irradiation;
65% With palladium 10% on activated carbon; oxygen; copper dichloride In tetrahydrofuran; water Reflux;
65% With potassium bromate; palladium 10% on activated carbon In tetrahydrofuran; water at 65℃; Typical experimental procedure for Wacker oxidation with 10% Pd0/C-KBrO3 General procedure: To the solution of olefine (1 mmol), in THF/water (4:1, 15 mL), 10% Pd/C (0.05 mmol) and KBrO3 (3 mmol) were added. This mixture was heated at reflux temperature. After completion of reaction (checked by TLC), the mixture was diluted with water and filtered through Whatman 40 filter paper. The filtrate was extracted with ethyl acetate. The combined organic layer washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography to get the product.
  • 37
  • [ 499-06-9 ]
  • [ 6656-60-6 ]
  • [ 2393-23-9 ]
  • [ 73789-56-7 ]
  • [ 1349839-37-7 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 3.25h;
  • 38
  • [ 499-06-9 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 140-75-0 ]
  • [ 1349839-28-6 ]
YieldReaction ConditionsOperation in experiment
84% In dichloromethane at 20℃; for 3.25h;
  • 39
  • [ 499-06-9 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1349839-14-0 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 3.25h;
  • 40
  • [ 499-06-9 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 104-84-7 ]
  • [ 1349839-15-1 ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 3.25h;
  • 41
  • [ 586-76-5 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1349839-30-0 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane at 20℃; for 3.25h;
  • 42
  • [ 6656-60-6 ]
  • [ 99-94-5 ]
  • [ 73789-56-7 ]
  • [ 104-84-7 ]
  • [ 1349839-24-2 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 3.25h;
  • 43
  • [ 6656-60-6 ]
  • [ 2393-23-9 ]
  • [ 73789-56-7 ]
  • [ 74-11-3 ]
  • [ 1349839-36-6 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane at 20℃; for 3.25h;
  • 44
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 140-75-0 ]
  • [ 88-65-3 ]
  • [ 1349839-29-7 ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane at 20℃; for 3.25h;
  • 45
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 74-11-3 ]
  • [ 1349839-32-2 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 3.25h;
  • 46
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 619-04-5 ]
  • [ 1349839-20-8 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane at 20℃; for 3.25h;
  • 47
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 619-04-5 ]
  • [ 104-84-7 ]
  • [ 1349839-16-2 ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane at 20℃; for 3.25h;
  • 48
  • [ 6656-60-6 ]
  • [ 104-94-9 ]
  • C17H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzene / 24 h / 20 °C / Molecular sieve; Inert atmosphere 2.1: sodium cyanoborohydride; acetic acid / methanol; benzene / 24 h / 20 °C 2.2: Saturated solution
  • 49
  • [ 6656-60-6 ]
  • [ 104-94-9 ]
  • [ 875540-93-5 ]
YieldReaction ConditionsOperation in experiment
64% With 2-Phenylbenzothiazolin; C51H59O4P In benzene at 20℃; for 48h; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 50
  • [ 6656-60-6 ]
  • [ 104-94-9 ]
  • C17H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In benzene at 20℃; for 24h; Molecular sieve; Inert atmosphere;
  • 51
  • [ 499-06-9 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 1431463-19-2 ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 1h;
85% In water at 20℃; for 1h; Green chemistry;
  • 52
  • [ 6656-60-6 ]
  • [ 99-94-5 ]
  • [ 73789-56-7 ]
  • [ 1431463-20-5 ]
YieldReaction ConditionsOperation in experiment
87% In water at 20℃; for 1h; Green chemistry;
85% In dichloromethane at 20℃; for 1h;
  • 53
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 619-04-5 ]
  • [ 1431463-21-6 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane at 20℃; for 1h;
83% In water at 20℃; for 1h; Green chemistry;
  • 54
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 74-11-3 ]
  • [ 1431463-22-7 ]
YieldReaction ConditionsOperation in experiment
85% In water at 20℃; for 1h; Green chemistry;
82% In dichloromethane at 20℃; for 1h;
  • 55
  • [ 586-76-5 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 1431463-23-8 ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 1h;
84% In water at 20℃; for 1h; Green chemistry;
  • 56
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 99-04-7 ]
  • [ 1431463-25-0 ]
YieldReaction ConditionsOperation in experiment
87% In water at 20℃; for 1h; Green chemistry;
85% In dichloromethane at 20℃; for 1h;
  • 57
  • [ 6656-60-6 ]
  • [ 619-64-7 ]
  • [ 73789-56-7 ]
  • [ 1431463-26-1 ]
YieldReaction ConditionsOperation in experiment
87% In water at 20℃; for 1h; Green chemistry;
84% In dichloromethane at 20℃; for 1h;
  • 58
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 637-44-5 ]
  • [ 1432747-02-8 ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane at 20℃; for 6h;
  • 59
  • [ 6656-60-6 ]
  • [ 2393-23-9 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 1432747-04-0 ]
YieldReaction ConditionsOperation in experiment
79% In dichloromethane at 20℃; for 6h;
  • 60
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 104-84-7 ]
  • [ 1432747-05-1 ]
YieldReaction ConditionsOperation in experiment
75% In dichloromethane at 20℃; for 6h;
  • 61
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 89-97-4 ]
  • 2-[(2-chlorobenzyl)amino]-2-[5-(2-phenyl-1-ethynyl)-1,3,4-oxadiazol-2-yl]propyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In dichloromethane at 20℃; for 6h;
  • 62
  • [ 617-89-0 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 1432747-11-9 ]
YieldReaction ConditionsOperation in experiment
77% In dichloromethane at 20℃; for 6h;
  • 63
  • [ 6850-57-3 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 1432747-10-8 ]
YieldReaction ConditionsOperation in experiment
71% In dichloromethane at 20℃; for 6h;
  • 64
  • [ 6656-60-6 ]
  • [ 118-31-0 ]
  • [ 73789-56-7 ]
  • [ 637-44-5 ]
  • [ 1432747-13-1 ]
YieldReaction ConditionsOperation in experiment
70% In dichloromethane at 20℃; for 6h;
  • 65
  • [ 6656-60-6 ]
  • [ 1615-02-7 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1557313-65-1 ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane at 20℃; for 6h;
  • 66
  • [ 6656-60-6 ]
  • [ 1866-39-3 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1557313-71-9 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 6h;
  • 67
  • [ 140-10-3 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1557313-58-2 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane at 20℃; for 6h;
  • 68
  • [ 6656-60-6 ]
  • [ 704-80-3 ]
  • [ 73789-56-7 ]
  • [ 100-46-9 ]
  • [ 1557313-61-7 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; for 6h;
  • 69
  • [ 6656-60-6 ]
  • [ 704-80-3 ]
  • [ 2393-23-9 ]
  • [ 73789-56-7 ]
  • [ 1557313-69-5 ]
YieldReaction ConditionsOperation in experiment
84% In dichloromethane at 20℃; for 6h;
  • 70
  • [ 6656-60-6 ]
  • [ 1866-38-2 ]
  • [ 73789-56-7 ]
  • [ 104-84-7 ]
  • [ 1557313-74-2 ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane at 20℃; for 6h;
  • 71
  • [ 140-10-3 ]
  • [ 6656-60-6 ]
  • [ 73789-56-7 ]
  • [ 104-84-7 ]
  • [ 1557313-52-6 ]
YieldReaction ConditionsOperation in experiment
89% In dichloromethane at 20℃; for 6h;
  • 72
  • [ 6656-60-6 ]
  • [ 704-80-3 ]
  • [ 73789-56-7 ]
  • [ 104-84-7 ]
  • [ 1557313-54-8 ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 6h;
  • 73
  • [ 931-53-3 ]
  • [ 6656-60-6 ]
  • [ 1866-39-3 ]
  • (E)-3-(cyclohexylamino)-2-methyl-3-oxo-2-(3-p-tolylacryloyloxy)propyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 74
  • [ 931-53-3 ]
  • [ 6656-60-6 ]
  • [ 459-32-5 ]
  • (E)-3-(cyclohexylamino)-2-(3-(4-fluorophenyl)acryloyloxy)-2-methyl-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 75
  • [ 931-53-3 ]
  • [ 6656-60-6 ]
  • [ 14755-02-3 ]
  • (E)-3-(cyclohexylamino)-2-(3-(3-hydroxyphenyl)acryloyloxy)-2-methyl-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 76
  • [ 931-53-3 ]
  • [ 6656-60-6 ]
  • [ 1895-97-2 ]
  • (E)-3-(cyclohexylamino)-2-methyl-2-(2-methyl-3-phenylacryloyloxy)-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 77
  • [ 931-53-3 ]
  • [ 6656-60-6 ]
  • [ 1866-38-2 ]
  • (E)-2-(3-(3-chlorophenyl)acryloyloxy)-3-(cyclohexylamino)-2-methyl-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 78
  • [ 7188-38-7 ]
  • [ 6656-60-6 ]
  • [ 459-32-5 ]
  • (E)-3-(tert-butylamino)-2-(3-(4-fluorophenyl)acryloyloxy)-2-methyl-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 79
  • [ 7188-38-7 ]
  • [ 6656-60-6 ]
  • [ 1895-97-2 ]
  • (E)-3-(tert-butylamino)-2-methyl-2-(2-methyl-3-phenylacryloyloxy)-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
  • 80
  • [ 7188-38-7 ]
  • [ 6656-60-6 ]
  • [ 1866-38-2 ]
  • (E)-3-(tert-butylamino)-2-(3-(3-chlorophenyl)acryloyloxy)-2-methyl-3-oxopropyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water for 0.666667h; Sonication; Green chemistry; 2.3. Ultrasound-promoted synthesis of propanamide derivatives(4 and 5) General procedure: The carboxylic acid derivative (2) (1.0 mmol), 2-oxopropyl benzoate (3) (1 mmol), isocyanide (1) (1 mmol) and water (7 mL) were added into a 25 mL round bottomed flask. The reaction mixture was sonicated under 100 W for the period of time (the reaction was monitored by TLC). The solvent was eliminated under decreased pressure, and the products were generated without any purification (4 and 5). The authenticity of the samples (4a-4i and 5a-5i) was established by their 1H NMR, 13C NMR, FT-IR, elemental analyses and MS. The characterization data of the compounds are given below:
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