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[ CAS No. 2517-43-3 ] {[proInfo.proName]}

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Product Details of [ 2517-43-3 ]

CAS No. :2517-43-3 MDL No. :MFCD00002931
Formula : C5H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JSGVZVOGOQILFM-UHFFFAOYSA-N
M.W : 104.15 Pubchem ID :17291
Synonyms :

Safety of [ 2517-43-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P370+P378-P403+P235-P501 UN#:1987
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2517-43-3 ]

* 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 [ 2517-43-3 ]

[ 2517-43-3 ] Synthesis Path-Downstream   1~52

  • 2
  • [ 2517-43-3 ]
  • [ 6937-34-4 ]
  • [ 4842-02-8 ]
  • 3
  • [ 2517-43-3 ]
  • [ 554-12-1 ]
  • (-)-3-methoxy-1-butyl propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With phosphate buffer for 20h; Ambient temperature; hog liver carboxylesterase catalyzed transesterification;
  • 4
  • [ 2517-43-3 ]
  • [ 38339-95-6 ]
  • [ 114614-51-6 ]
YieldReaction ConditionsOperation in experiment
76% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran
  • 5
  • [ 2517-43-3 ]
  • [ 5281-76-5 ]
YieldReaction ConditionsOperation in experiment
71% With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
With perchloric acid; N-bromoacetamide In water; acetic acid at 303℃; other temperatures; ΔH(excit.), ΔS(excit.), ΔF(excit.);
With pyridinium chlorochromate In dimethyl sulfoxide for 6h; Εa, log A, ΔS(excit.), ΔG(excit.);
With acetic acid; bromamine B In water at 29.9℃; ΔH(excit.), ΔS(excit.), ΔG(excit.); solvent isotope effect;
With perchloric acid; sodium N-chloromethylcarbamate In water at 29.9℃; further temperatures, further objects of study: ΔH(activ.), ΔS(activ.), ΔG(activ.);
With perchloric acid; 3,5-Dinitro-N-brombenzamid In water; acetic acid at 14.9℃; for 12h; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.); various solvent ratio;
With N-Chlorourethan In acetic acid at 19.9℃; ΔH(excit.), ΔS(excit.), ΔG(excit.); var. temps.;
With perchloric acid; chloramine-B In water; acetic acid at 24.9 - 39.9℃; ΔH(excit.), ΔS(excit.), ΔG(excit.);
With 2,2'-bipyridinium chlorochromate In dimethyl sulfoxide at 29.9 - 59.9℃; ΔH(excit.), ΔS(excit.), ΔG(excit.);
With PBC In dimethyl sulfoxide at 24.9℃; for 10h; mechanism;
With 2,2'-bipyridinium chlorochromate In dimethyl sulfoxide for 10h;
With quinolinium monofluorochromate(VI) In dimethyl sulfoxide at 34.85℃;
With HMTAB In acetic acid for 10h;
With benzyltrimethylammonium chlorobromate In water; acetic acid at 14.85℃; for 12h;
With quinolinium bromochromate In dimethyl sulfoxide at 24.85℃; for 10h;
With butyltriphenylphosphonium dichromate; toluene-4-sulfonic acid In dimethyl sulfoxide at 54.84℃; for 10h; Darkness;
With tetrakis pyridine silver dichromate In dimethyl sulfoxide at 34.84℃;
With morpholinium chlorochromate In dimethyl sulfoxide at 24.84℃; for 10h; Darkness;
With pyridinium chlorochromate In dichloromethane at 18 - 22℃; for 3h; 13.1 To a suspension of P00 (4.75 g, 22.0 mmol, Aldrich) in DCM (70 mL) is added a solution of 3- methoxy-1 -butanol (1 .5 g, 14.4 mmol) in 30 mL of DCM. The reaction is stirred at RT for 3 hours. The mixture is diluted in DCM and the residue is removed by filtration. The filtrate is concentrated and purified by Combif lash (90:10 Hex/EtOAc) to afford 13a.

Reference: [1]Muenster, Niels; Harms, Klaus; Koert, Ulrich [Chemical Communications, 2012, vol. 48, # 13, p. 1866 - 1867]
[2]Mukherjee, Jogeshwar; Banerji, Kalyan K. [Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2323 - 2326]
[3]Banerji, Kalyan, K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 7, p. 650 - 652]
[4]Mathur, Abha; Banerji, Kalyan K. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1645 - 1648]
[5]Negi, S. C.; Mathur, Abha; Banerji, Kalyan K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1987, vol. 26, # 5, p. 399 - 401]
[6]Kothari, Seema; Agarwal, Anupma; Banerji, Kalyan K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 8, p. 722 - 724]
[7]Grover, Anjali; Varshney, Seema; Banerji, Kalyan K. [Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 629 - 632]
[8]Shah, Bindu; Jain, Anandi L.; Banerji, Kalyan K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1982, vol. 21, # 7, p. 720 - 722]
[9]Loonker, Kavita; Sharma, Pradeep K.; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1997, # 7, p. 1663 - 1680]
[10]Rao, P. Surya Chandra; Suri, Deepa; Kothari, Seema; Banerji, Kalyan K. [International Journal of Chemical Kinetics, 1998, vol. 30, # 4, p. 285 - 290]
[11]Loonker, Kavita; Sharma, Pradeep K.; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1997, # 7, p. 1663 - 1680]
[12]Choudhary, Kirti; Sharma, Pradeep K.; Banerji, Kalyan K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1999, vol. 38, # 4, p. 325 - 330]
[13]Gangwani, Hemlata; Sharma, Pradeep K.; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1999, # 3, p. 854 - 871]
[14]Bhatt, Monica; Sharma, Pradeep K.; Banerji, Kalyan K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 826 - 831]
[15]Vyas, Shweta; Sharma, Pradeep K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2004, vol. 43, # 6, p. 1219 - 1223]
[16]Location in patent: experimental part Panday, Dinesh; Kothari, Seema [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 918 - 925]
[17]Location in patent: experimental part Meena; Daiya; Sharma; Banerji; Kotai; Sharma, Vinita [Journal of the Indian Chemical Society, 2011, vol. 88, # 12, p. 1887 - 1893]
[18]Location in patent: experimental part Barthora; Baghmar; Agarwal; Sharma, Vinita [Journal of the Indian Chemical Society, 2011, vol. 88, # 5, p. 677 - 683]
[19]Current Patent Assignee: MEDIVIR AB - WO2015/65336, 2015, A1 Location in patent: Page/Page column 28; 29
  • 6
  • [ 2517-43-3 ]
  • (+)-3-methoxy-1-butanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With phosphate buffer; propanoic acid methyl ester for 20h; Ambient temperature;
  • 7
  • [ 93185-29-6 ]
  • [ 2517-43-3 ]
YieldReaction ConditionsOperation in experiment
80% With lithium aluminium tetrahydride In diethyl ether for 2h; Ambient temperature;
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; diethyl ether
  • 9
  • [ 2517-43-3 ]
  • [ 18880-00-7 ]
  • [ 877-65-6 ]
  • [ 56428-01-4 ]
  • 4-tert-butylbenzyl 3-methoxybutyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 6% 3: 4% With sodium hydroxide at 60℃; for 3h;
  • 10
  • [ 2517-43-3 ]
  • 4-(3-pyrazolyl)phenol [ No CAS ]
  • 3-[4-(3-methoxybutoxy)phenyl]pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h;
  • 12
  • [ 2517-43-3 ]
  • 3-(1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-1-(3-methoxy-butyl)-1<i>H</i>-quinolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisopropyl azodicarboxylate; Ph3P / CH2Cl2 / 20 °C 2.1: NaH / tetrahydrofuran / 1.5 h / Heating 2.2: 388 mg / acetic acid / tetrahydrofuran / 1 h / Heating
  • 13
  • [ 2517-43-3 ]
  • (-)-3-methoxy-1-butanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / 0.1 M phosphate buffer / 20 h / Ambient temperature; hog liver carboxylesterase catalyzed transesterification 2: 48 percent / H2O, KCl / acetone
  • 14
  • [ 1120-97-4 ]
  • [ 2517-43-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / ZnCl2 / pentane / 1 h 2: 80 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature
  • 15
  • [ 2517-43-3 ]
  • [ 3540-60-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: Et3N / benzene / Heating
  • 16
  • [ 108-05-4 ]
  • (PPh3)2 PdCl2 [ No CAS ]
  • L-3-methoxy-1-butyl acetyl-L-lactate [ No CAS ]
  • [ 2517-43-3 ]
  • [ 10326-41-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; CO In tetrahydrofuran 7 EXAMPLE 7 EXAMPLE 7 A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), (PPh3)2 PdCl2 (0.05 mmol), L-3-methoxy-1-butanol (0.5 mmol), and vinyl acetate (0.5 mmol). The reactor is sealed, pressurized to 1000 psig with CO, and stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a diastereomeric mixture of L-3-methoxy-1-butyl acetyl-L-lactate and L-3-methoxy-1-butyl acetyl-D-lactate. The diastereomers are separated by preparative gas chromatography using an SE-30 liquid phase column. Each diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C. to give pure L- and D-lactic acid, acetic acid, and L-3-methoxy-1-butanol, which is thereafter recycled to a repeat of the foregoing hydrocarboxylation reaction.
With hydrogenchloride; CO In tetrahydrofuran 8 EXAMPLE 8 EXAMPLE 8 A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), (PPh3)2 PdCl2 (0.05 mmol), D-3-methoxy-1-butanol (0.5 mmol), and vinyl acetate (0.5 mmol). The reactor is sealed, pressurized to 1000 psig with CO, and stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a diastereomeric mixture of D-3-methoxy-1-butyl acetyl-L-lactate and D-3-methoxy-1-butyl acetyl-D-lactate. The diastereomers are separated by preparative gas chromatography using an SE-30 liquid phase column. Each diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C. to give pure L- and D-lactic acid, acetic acid, and D-3-methoxy-1-butanol, which is thereafter recycled to a repeat of the foregoing hydrocarboxylation reaction.
  • 17
  • [ 124-09-4 ]
  • [ 2517-43-3 ]
  • [ 111-49-9 ]
YieldReaction ConditionsOperation in experiment
14 EXAMPLE 14 EXAMPLE 14 A 2-liter flask was charged with 450 g of 3-methoxybutanol and 60 g of Raney nickel, and with vigorous stirring, the temperature was maintained at 105° C. A 25% 3-methoxybutanol solution of hexamethylenediamine was added dropwise in an amount of 500 g over the course of 3 hours. The reaction pressure was adjusted to 180 mmHg using a vacuum pump, and hydrogen was not affirmatively supplied at all to the reaction system. As soon as the hexamethylenediamine solution began to be added dropwise, the reaction was initiated. The resulting hexamethyleneimine evaporated off together with the 3-methoxybutanol solvent. It was liquefied by a condenser, and then collected. The by-product ammonia gas was removed using a vacuum pump. After adding all of the hexamethylenediamine solution, the reaction was performed for an additional 30 minutes.
  • 18
  • [ 2517-43-3 ]
  • [ 38339-95-6 ]
  • [ 1972-28-7 ]
  • [ 114614-51-6 ]
YieldReaction ConditionsOperation in experiment
1.17 g (52%) With ammonium hydroxide; triphenylphosphine In tetrahydrofuran; methanol; dichloromethane 72 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-methoxybut-1-yl)oxybenzamid EXAMPLE 72 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-methoxybut-1-yl)oxybenzamid A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C. Anal. Calc'd. for C18 H30 ClN3 O3: C, 58.13; H, 8.13; N, 11.30; Cl, 9.53. Found: C, 58.43; H, 8.35; N, 11.33; Cl, 9.70.
  • 19
  • [ 2517-43-3 ]
  • [ 124-63-0 ]
  • [ 105-53-3 ]
  • ethyl 5-methoxy-2-ethoxycarbonylcaprylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium methylate In ethanol; benzene 8 Example 8 Example 8 (Production of 5-methoxy-1-hexanol) To 100 g of 3-methoxy-1-butanol, 187 ml of pyridine and 374 ml of benzene were added, and under stirring, 132 g of methanesulfonyl chloride was added below 10°C in 60 min. After 15 min. of stirring at that temperature, the mixture was raised in temperature to 15 - 21°C and stirred for 3 hours. The mixture was poured into cold water and extracted with benzene. The benzene extract was washed with 5 %-hydrochloric acid and water, dried and subjected to distillation of benzene to obtain 173 g of a pale yellow liquid. Then, 59.4 g of 95 % sodium methoxide was added to 220 ml of ethanol, and under stirring, 243 g of diethyl malonate was added thereto at 25 - 30°C in 60 min. After further, 30 min. of stirring, 173 g of the above pale yellow liquid was dropped at 30 - 36°C in 60 min. The mixture was further stirred for 18 hours with refluxing at 80 - 82°C. After the reaction, icewater was poured, and the product was extracted with benzene, washed with water and dried. By distilling off the solvent and effecting vacuum distillation to obtain 190 g of ethyl 5-methoxy-2-ethoxycarbonylcaprylate.
  • 20
  • [ 2517-43-3 ]
  • [ 108-46-3 ]
  • [ 89-86-1 ]
YieldReaction ConditionsOperation in experiment
95.4% With hydrogenchloride; sodium hydroxide; CO2 In water 4 Example 4 Example 4 165.2g (1.50 mole) of resorcinol, 100g (2.50 mole) of sodium hydroxide and 483g of 3-methoxy-1-butanol are added to the same reaction instrument as Example 1 and reacted together at a temperature of between 140 and 150°C for 3 hours maintaining 3 atm of CO2. The reaction mixture is filtered at 130 to 140°C, the filtered precipitates is dissolved in 550 g of water, and neutralised by 250g of concentrated HCl. The white solid thus obtained is 220.5g (1.43 mole, yield 95.4%) of 2,4-dihydroxybenzoic acid, having a melting point of from 225 to 226°C.
87.4% With CO2; potassium carbonate In water 2 Example 2 Example 2 105.2g (0.96 mole) of resorcinol, 200.2g (1.45 mole) of potassium carbonate and 501 g of 3-methoxy-1-butanol (solvent 2) are added to the same reaction instrument as Example 1, heated to 95 to 105°C reacted for 2 hours maintaining 5 atm of CO2. The reaction mixture is filtered at 95 to 105°C, and the filtrate is used in Example 3. The filtered precipitate is dissolved in 400 g of water, and neutralized by 190 g of concentrated. The white solid thus obtained is 128.7 g (0.84 mole, yield 87.4%) of 2,4-dihydroxybenzoic acid, having a melting point of from 224 to 225°C.
  • 21
  • [ 2517-43-3 ]
  • [ 124-63-0 ]
  • [ 428870-98-8 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In ethyl acetate at 2 - 20℃; for 3.5h; 1 To an ethyl acetate (AcOEt) solution containing 200 g (1.92 mol) of 3-methoxy-l-butanol, added was 185 g (1.83 mol) of triethylamine (Et3N). After the reaction system was cooled to 2°C, 209 g (1.83 mol) of methanesulfonic acid chloride (MsCl) was added dropwise to the reaction system, while the temperature of the reaction system was kept at 15°C or lower After the dropwise addition was completed, the reaction system was stirred at 100C or lower for 30 minutes, and then the temperature of the reaction system was raised to the room temperature, followed by stirring for 3 hours. Water was added thereto, to separate the reaction solution, and the separated organic phase was washed with water, 1 -N aqueous hydrochloric acid, and water, in this order The resulting organic phase was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain 292 2 g of a crude intermediate (1-A) (yield 88%).
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice bath; 7 Production Example 73-Methoxybutyl methanesulfonate To a dichloromethane (30 mL) mixture of 3-methoxy-1-butanol (3.12 g, 30.0 mmol) and triethylamine (4.62 mL, 33.0 mmol), was added methanesulfonyl chloride (4.62 mL, 33.0 mmol) while stirring on ice, and the mixture was stirred at room temperature for 30 minutes. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was then distilled off under reduced pressure.1H-NMR (CDCl3) δ: 1.18 (d, J=6.0 Hz, 3H), 1.80-1.92 (m, 2H), 3.00 (s, 3H), 3.33 (s, 3H), 3.43-3.52 (m, 1H), 4.26-4.42 (m, 2H).
  • 22
  • [ 2517-43-3 ]
  • 2-[4-((R)-3-dimethylamino-pyrrolidin-1-yl)-3-fluorophenyl]-6-(3-methoxy-butoxy)-3,4-dihydro-2H-isoquinolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-[4-((R)-3-dimethylaminopyrrolidin-1-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one In tetrahydrofuran for 0.25h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran for 0.166667h; Stage #3: 3-methoxy butanol In tetrahydrofuran for 12h; 212.Y Example 2122-[4-((R)-3-Dimethylamino-pyrrolidin-1-yl)-3-fluorophenyl]-6-(3-methoxy-butoxy)-3,4- dihydro-2H-isoquinolin-1-one Method Y; A mixture of triphenylphosphine (polymer; 156 mg), 2-[4-((R)-3-dimethylamino- pyrrolidin-1 -yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1 -one (0.10 g) and THF (7 ml_) was stirred for 15 minutes. Then di-tert-butyl-azodicarboxylate (0.10 g) in THF (1 ml_) was added, stirring for a further 10 minutes. Then 3-methoxy-butan-1-ol (35 mg) was added and it was stirred for 12 hours. It was sucked off of the polymer and the filtrate was concentrated. The residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 455.58 (C26H34FN3O3); MS (ESI): 456 (M+H+).
  • 23
  • [ 2517-43-3 ]
  • [ 563-43-9 ]
  • 0.76[Cl2Al(OCH2CH2CHCH3OCH3)]2*0.24[Cl2Al(OCH2CH2CHCH3OCH3)]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In hexane (Ar); slow addn. of a soln. of alcohol in hexane to a soln. of aluminiumcompd. in hexane at 0°C; evapn., drying in vac., crystn. (C6H6, 10°C, 1 wk); elem. anal.;
  • 24
  • [ 2517-43-3 ]
  • [ 358-23-6 ]
  • [ 1018073-58-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine In chloroform for 0.25h; Inert atmosphere; Cooling with ice; 170.170-1 Step 170-1: Pyridine (2.91 mL) and Tf2O (4.85 mL) were added to a solution of 3-methoxy-1-butanol (2.50 g) in CHCl3 (50.0 mL) under nitrogen atmosphere with ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. H2O was added to the reaction solution with ice-cooling, followed by extraction with CHCl3. The organic layer was washed with H2O three times, dried over Na2SO4 and then concentrated under reduced pressure to obtain a crude pale brown oily compound (2.86 g).
  • 25
  • [ 2517-43-3 ]
  • [ 372-09-8 ]
  • 3-methoxybutyl 2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: cyanoacetic acid With trifluoroacetic anhydride In acetonitrile at 22℃; for 3h; Inert atmosphere; Stage #2: 3-methoxy butanol In acetonitrile at 22℃; for 3h; 2 Example 2; - One pot process (comprising the first and second process of the present invention); To a solution of TFAA (22.4g, 107mmol) in acetonitrile (100 mL) was added 2-cyanoacetic acid (20g, 235 mmol). The mixture was stirred for 3 h at 22°C under a dry atmosphere. The formation of the 2-cyanoacetic anhydride was verified by NMR (s, 3.85ppm). A solution of 3- methoxybutanol (10g, 96mmol) in acetonitrile (30 mL) was added dropwise (10 min). A slight exotherm was noted. The pale yellow mixture was stirred at 22°C for 3 h. The solvents were removed in vacuo and the resulting yellow oil taken up in 100mL of methylene chloride. The solution was neutralized by the addition of aq. sat. sodium bicarbonate. The aqueous layer was separated and extracted with 50 mL of methylene chloride. The combined organics were dried over MgS04 and reduced to afford a pale yellow liquid, 15g (91 % ) which had a purity of 98.4% by GC.1 H NMR: 4.31 (2H, t, J=7, 1), 3.91 (2H, s), 3.57 (1 H, qt, J =6.1 , J=3.8), 3.4 (s, 3H), 2.0 (2H, td, J=7.1 , J=3.8), 1.133 (3H, d, J=6.1).
In toluene Reflux; 3 Para-toluenesulfonic acid, PTS, (0.2 g) was added to a toluene solution (200 mL) of compound (2-A) (37 g, 0.44 mmol) and 2-methoxy butanol (2-B) (46 g, 0.44 mol), and dehydrated during refluxing with Dean-Stark. After the termination of the reaction, toluene was evaporated from the resultant solution. The resultant was cooled by the room temperature, and extracted by adding ethyl acetate and water. The obtained organic layer was washed by adding water, saturated aqueous solution of sodium hydrogen carbonate, 1N-hydrochloric and water in sequence. The organic layer was dried by adding magnesium sulfate, and, after evaporation of the solvent under the reduced pressure, 65 g of the crude product, compound (2-C), was obtained.
  • 26
  • [ 2517-43-3 ]
  • [ 2991-42-6 ]
  • 3-methoxybutyl 4-(trifluoromethyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine at 20℃; for 3.5h;
40% In pyridine 3-methoxybutyl 4-(trifluoromethyl)benzenesulfonate (13) 3-methoxybutyl 4-(trifluoromethyl)benzenesulfonate (13) To a solution of 3-methoxybutane-1-ol (12) (0.58 g, 4.9 mmol) in pyridine (5 mL) was added p-(trifluoromethyl)-benzenesulfonyl chloride (0.98 g, 4 mmol). The solution was stirred at rt for 3.5 h. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with 1 M HCl (6*25 mL), saturated aqueous NaHCO3 (1*25 mL) and saturated aqueous NaCl (1*25 mL). The organics were dried over Na2SO4 and concentrated to give an oil (13) (0.53 g, 40%). 1H NMR (400 MHz CDCl3) δ 8.03 (d, 2H, J=8.1 Hz), 7.81 (d, 2H, J=8.3 Hz), 4.19 (m, 2H), 3.35 (m, 1H), 3.18 (s, 3H), 1.78 (m, 2H), 1.09 (d, 3H, J=6.0 Hz); 19F δ (s). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 45.99; H, 4.64.
  • 27
  • [ 2517-43-3 ]
  • [ 832-53-1 ]
  • 3-methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With triethylamine In dichloromethane at 20℃; for 4h;
  • 28
  • [ 2517-43-3 ]
  • [ 776-04-5 ]
  • 3-methoxybutyl 2-(trifluoromethyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine In dichloromethane at 20℃; for 2h;
With triethanolamine In dichloromethane 3-Methoxybutyl 2-(trifluoromethyl)benzenesulfonate 3-Methoxybutyl 2-(trifluoromethyl)benzenesulfonate To a solution of 3-methoxybutane-1-ol (0.63 g, 6.0 mmol) and TEA (0.42 g, 4.1 mmol), in CH2Cl2 (5 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (0.50 g, 2.0 mmol). The solution was stirred at rt for 2 h. The reaction mixture was diluted with CH2Cl2 (15 mL) and washed with 1 M HCl (3*15 mL), saturated aqueous NaHCO3 (1*15 mL) and saturated aqueous NaCl (1*15 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography with ethyl acetate in hexanes yielded the desired product (0.34 g, 50%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.75 (m, 2H), 4.24 (m, 2H), 3.40 (m, 1H), 3.21 (s, 3H), 1.80 (m, 2H), 1.10 (d, 3H, J=6.2 Hz). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 46.30; H, 4.88.
  • 29
  • [ 2517-43-3 ]
  • [ 372-09-8 ]
  • [ 407-25-0 ]
  • [ 340034-46-0 ]
  • 3-methoxybutyl 2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: cyanoacetic acid; trifluoroacetic anhydride In acetonitrile at 22℃; for 3h; Inert atmosphere; Stage #2: 3-methoxy butanol In acetonitrile at 22℃; for 3h; 2 Comparative example 2 - (acetonitrile reaction mixture containing trifluoroacetic acid anhydride and 2-cyanoacetic acid in a molar ratio of 1 : 1); To a solution of trifluoroacetic acid anhydride (11.2 g, 53.2 mmol) in acetonitrile (30 mL) was added 2-cyanoacetic acid (4.5 g, 53.2 mmol). The mixture was stirred for 3 h at 22°C under a dry atmosphere. A solution of 3-methoxybutanol (5.0 g, 48.5 mmol) in dry acetonitrile (20 mL) was added dropwise. The mixture was stirred for at 22°C for 3 h. The solvents were removed in vacuo and the resulting yellow oil taken up in 50 mL of methylene chloride. The solution was neutralized by the addition of aq. sat. sodium bicarbonate. The aqueous layer was separated and extracted with 50 mL of methylene chloride. The combined organics were dried with magnesium sulfate and reduced in vacuo to afford 8.1 g of a pale yellow liquid. GCMS revealed this to be a 78.5/21.5% mixture of 3-methoxybutyl cyanoacetate and 3-methoxybutyl trifluoroacetate.
  • 30
  • [ 2517-43-3 ]
  • [ 70776-23-7 ]
  • [ 1355052-78-6 ]
  • 3-methoxybutyl 2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 50℃; for 2h; 1.2 Example 1; First process; To a solution of trifluoroacetic acid anhydride (19.95 g, 95 mmol) in acetonitrile (30 ml) was added 2-cyanoacetic acid (19.38 g, 228 mmol). The mixture was stirred for 5h under a nitrogen atmosphere at 22°C. The resulting yellow solution was reduced in vacuo to afford 18.6 g of a yellow oil. By NMR analysis the yellow oil was identified as a 10: 1 :6 mixture a of 2-cyanoactic anhydride: 2-cyanoacetic trifluoroacetic anhydride : 2- cyanoacetic acid.Second process; The yellow oil of the first process was dissolved in dry acetonitrile (20 mL) and added dropwise to a mixture of 3-methoxybutanol (7.6g, 73 mmol) and poly(4-vinyl pyridine) (13 g, 124 mmol) as a catalyst at 50°C. The resulting mixture was stirred for 2 h at 50 °C. The solvents were removed under reduced pressure and the resulting residue was dissolved in methylene chloride (100 mL) and filtered. The filter cake was washed with a 1 :1 mixture (50 mL) of methylene chloride and ethyl acetate and the combined organic phase was washed with sat. aq. NaHC03 and brine (50 mL each) and then dried over MgS04. The solvents and volatile components were removed under reduced pressure to afford 11.9 (95%) g of 3-methoxybutyl 2-cyanoacetic ester (purity of 95%, as determined by GC).1 H NMR: 4.31 (2H, t, J=7,1), 3.91 (2H, s), 3.57 (1 H, qt, J =6.1 , J=3.8), 3.4 (s, 3H), 2.0 (2H, td, J=7.1 , J=3.8), 1.133 (3H, d, J=6.1).
In acetonitrile at 50℃; for 2h; 1.2 Second process The yellow oil of the first process was dissolved in dry acetonitrile (20 mL) and added dropwise to a mixture of 3-methoxybutanol (7.6g, 73 mmol) and poly(4-vinyl pyridine) (13 g, 124 mmol) as a catalyst at 50°C. The resulting mixture was stirred for 2 h at 50 °C. The solvents were removed under reduced pressure and the resulting residue was dissolved in methylene chloride (100 mL) and filtered. The filter cake was washed with a 1:1 mixture (50 mL) of methylene chloride and ethyl acetate and the combined organic phase was washed with sat. aq. NaHCO3 and brine (50 mL each) and then dried over MgSO4. The solvents and volatile components were removed under reduced pressure to afford 11.9 (95%) g of 3-methoxybutyl 2-cyanoacetic ester (purity of 95%, as determined by GC). 1H NMR: 4.31 (2H, t, J=7,1), 3.91 (2H, s), 3.57 (1H, qt, J =6.1, J=3.8), 3.4 (s, 3H), 2.0 (2H, td, J=7.1, J=3.8), 1.133 (3H, d, J=6.1).
  • 31
  • [ 2517-43-3 ]
  • [ 70776-23-7 ]
  • 3-methoxybutyl 2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 22℃; for 3.16667h; 2 Example 2 - One pot process (comprising the first and second process of the present invention) To a solution of TFAA (22.4g, 107mmol) in acetonitrile (100 mL) was added 2-cyanoacetic acid (20g, 235 mmol). The mixture was stirred for 3 h at 22°C under a dry atmosphere. The formation of the 2-cyanoacetic anhydride was verified by NMR (s, 3.85ppm). A solution of 3-methoxybutanol (10g, 96mmol) in acetonitrile (30 mL) was added dropwise (10 min). A slight exotherm was noted. The pale yellow mixture was stirred at 22°C for 3 h. The solvents were removed in vacuo and the resulting yellow oil taken up in 100mL of methylene chloride. The solution was neutralized by the addition of aq. sat. sodium bicarbonate. The aqueous layer was separated and extracted with 50 mL of methylene chloride. The combined organics were dried over MgSO4 and reduced to afford a pale yellow liquid, 15g (91%) which had a purity of 98.4% by GC. 1H NMR: 4.31 (2H, t, J=7,1), 3.91 (2H, s), 3.57 (1H, qt, J =6.1, J=3.8), 3.4 (s, 3H), 2.0 (2H, td, J=7.1, J=3.8), 1.133 (3H, d, J=6.1).
  • 32
  • [ 2517-43-3 ]
  • [ 832-53-1 ]
  • [ 144-55-8 ]
  • 3-methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With triethanolamine In dichloromethane; ethyl acetate 3-Methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate 3-Methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate To a solution of 3-methoxybutane-1-ol (0.78 g, 7.5 mmol) and TEA (0.388 g, 3.8 mmol), in CH2Cl2 (15 mL) was added pentafluorobenzenesulfonyl chloride (0.79 g, 3.0 mmol). The solution was stirred at rt for 4 h. Saturated aqueous NaHCO3 (10 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (30 mL) and washed with 0.5 M HCl (2*20 mL) and saturated aqueous NaCl (1*20 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography (15% ethyl acetate in hexanes) yielded the desired product (0.39 g, 36%). 1H NMR (400 MHz CDCl3) δ 4.40 (m, 2H), 3.45 (m, 1H), 3.26 (s, 3H), 1.87 (m, 2H), 1.15 (d, 3H, J=6.1 Hz). Anal. Calcd. For C11H11F5O4S: C, 39.53; H, 3.32. Found: C, 39.83; H, 3.45.
  • 33
  • [ 2517-43-3 ]
  • [ 1441119-58-9 ]
  • ethyl 2-diazo-3-[(3-methoxybutoxy)(methyl)amino]-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 25h; Inert atmosphere;
  • 34
  • [ 2517-43-3 ]
  • [ 111-66-0 ]
  • [ 201230-82-2 ]
  • C14H28O3 [ No CAS ]
  • C14H28O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; palladium dichloride; 2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In toluene at 100℃; for 20h; Overall yield = 94 %; regioselective reaction;
  • 35
  • [ 2517-43-3 ]
  • [ 110-82-7 ]
  • [ 201230-82-2 ]
  • C12H22O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With 1,10-Phenanthroline; di-tert-butyl peroxide; copper dichloride at 120℃; for 24h; Autoclave; Inert atmosphere;
  • 36
  • [ 75-15-0 ]
  • [ 2517-43-3 ]
  • potassium 3-methoxy-1-butylxanthate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.3% Stage #1: 3-methoxy butanol With potassium hydroxide at 20℃; for 2h; Stage #2: carbon disulfide
  • 37
  • [ 2517-43-3 ]
  • 2-((3-methoxybutyl)thio)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; iodine; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0 - 20 °C / Inert atmosphere
  • 38
  • [ 2517-43-3 ]
  • C5H11IO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere;
  • 39
  • [ 2517-43-3 ]
  • 2-((3-methoxybutyl)sulfonyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; iodine; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0 - 20 °C / Inert atmosphere 3: Oxone; hydrogenchloride / water; methanol / 20 °C
  • 40
  • [ 2517-43-3 ]
  • 2-((3-methoxybutyl)sulfonyl)benzenediazonium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; iodine; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0 - 20 °C / Inert atmosphere 3: Oxone; hydrogenchloride / water; methanol / 20 °C 4: sodium nitrite / water / 0 °C / Inert atmosphere
  • 41
  • [ 2517-43-3 ]
  • [ 629-05-0 ]
  • [ 201230-82-2 ]
  • C14H26O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With methanesulfonic acid; C29H33N2P; palladium dichloride In acetonitrile Glovebox; Sealed tube; Inert atmosphere; Autoclave; regioselective reaction; 2.4 Catalytic carbonylations of alkynes using ligand L3 or complex Pd(L3)Cl2 General procedure: In the glove box, a 4mL screw-cap vial was charged with Pd-catalyst (1.0mol%), ligand L3 (4.0mol%), methanesulfonic acid (MSA) (6.0mol%), solvent (1 mL), and an oven-dried stirring bar. After stirring for 15min, alkyne (0.5mmol) and alcohols (1.0mmol) were injected into the vial. The vial was closed by PTFE/white rubber septum (Wheaton 13mm Septa) and phenolic cap, and connected with atmosphere with a needle, and fixed in an alloy plate, and put into the autoclave (250mL) under argon atmosphere. At room temperature, the autoclave was flushed with CO gas five times and pressurized with CO gas to 30bar. The reaction was performed at 80°C for 12h. After that, the autoclave was cooled to room temperature and the pressure was carefully released. Hexadecane was added as an internal standard. A sample of the mixture was taken and analyzed by GC-FID (Shimadzu GC-2010) and GC-MS (Agilent GC-MS 7890A-5975C). Pure product could be obtained by column chromatography on silica gel using petroleum ether/ethyl acetate as eluents with a gradient ratio of 100:1-50:1.
  • 42
  • [ 2517-43-3 ]
  • [ 201230-82-2 ]
  • [ 693-02-7 ]
  • C12H22O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With methanesulfonic acid; C29H33N2P; palladium dichloride In acetonitrile Glovebox; Sealed tube; Inert atmosphere; Autoclave; regioselective reaction; 2.4 Catalytic carbonylations of alkynes using ligand L3 or complex Pd(L3)Cl2 General procedure: In the glove box, a 4mL screw-cap vial was charged with Pd-catalyst (1.0mol%), ligand L3 (4.0mol%), methanesulfonic acid (MSA) (6.0mol%), solvent (1 mL), and an oven-dried stirring bar. After stirring for 15min, alkyne (0.5mmol) and alcohols (1.0mmol) were injected into the vial. The vial was closed by PTFE/white rubber septum (Wheaton 13mm Septa) and phenolic cap, and connected with atmosphere with a needle, and fixed in an alloy plate, and put into the autoclave (250mL) under argon atmosphere. At room temperature, the autoclave was flushed with CO gas five times and pressurized with CO gas to 30bar. The reaction was performed at 80°C for 12h. After that, the autoclave was cooled to room temperature and the pressure was carefully released. Hexadecane was added as an internal standard. A sample of the mixture was taken and analyzed by GC-FID (Shimadzu GC-2010) and GC-MS (Agilent GC-MS 7890A-5975C). Pure product could be obtained by column chromatography on silica gel using petroleum ether/ethyl acetate as eluents with a gradient ratio of 100:1-50:1.
  • 43
  • [ 120-72-9 ]
  • [ 2517-43-3 ]
  • [ 527-31-1 ]
  • 3-methoxybutyl 2-(1H-indol-3-yl)-2-oxoacetate [ No CAS ]
  • 44
  • [ 2517-43-3 ]
  • dichloro{bis[2-(diphenylphosphino)ethyl]amine}ruthenium(II) dimer [ No CAS ]
  • [ 1295649-40-9 ]
YieldReaction ConditionsOperation in experiment
84.6% With sodium methylate; for 1h;Inert atmosphere; Reflux; A 50 mL four-necked round-bottomed flask equipped with a magnetic stirring bar, condenser, Claisen distillation apparatus, thermometer, and a three-way stopcock was evacuated and filled with nitrogen gas. Then, 8 3-methoxy-1-butanol (boiling point: 157 C., 30 mL), NaOMe (purity: 99.1 mass %, 391 mg, 7.17 mmol, 2.2 equivalents), and dichloro{bis[2-(diphenylphosphino)ethyl]amine}ruthenium(II) dimer (4B-1) (4.0 g, 3.26 mmol, 1.0 equivalent) obtained in the first step were charged into the flask successively. The resulting orange suspension was stirred under reflux for 1 hour while distilling off low-boiling-point compounds by means of the Claisen distillation apparatus. (Post-Treatment, Isolation, and Purification) The light brown suspension obtained after the reaction was cooled to 5 C. by using an ice-water bath and filtered by suction, and the obtained crystal was washed with methanol, water and methanol successively and dried by heating under reduced pressure to give 3.35 g of the title compound (1B-1) as a light yellow powder. Isolated yield: 84.6%. The NMR measurement results of this compound were consistent with those obtained in Example 1-1.
  • 45
  • [ 52462-29-0 ]
  • [ 2517-43-3 ]
  • [ 66534-97-2 ]
  • [ 1295649-40-9 ]
YieldReaction ConditionsOperation in experiment
76.6% A 100 mL four-necked round-bottomed flask equipped with a magnetic stirring bar, condenser, Claisen distillation apparatus, thermometer, and a three-way stopcock was evacuated and filled with nitrogen gas. Then, 3-methoxy-1-butanol (boiling point: 157 C., 60 mL), sodium methoxide (NaOMe) (purity: 99.1 mass %, 1.53 g, 28.08 mmol, 4.3 equivalents), and bis[2-(diphenylphosphino)ethyl]amine hydrochloride (3B-1_HCl) (6.56 g, 13.71 mmol, 2.1 equivalents) were charged into the flask successively. The obtained white suspension was stirred at room temperature for 30 minutes, and a neutralization reaction thereby proceeded while precipitating 10 sodium chloride, and as a result, a mixture of bis[2-(diphenylphosphino)ethyl]amine (3B-1) (2.1 equivalents) and NaOMe (2.2 equivalents) was obtained as a white suspension. Dichloro(p-cymene)ruthenium(II) dimer (2B-1) (4.0 g, 6.53 mmol, 1.0 equivalent) was added to the suspension above, and the resulting orange suspension was stirred under reflux for 1 hour while distilling off low-boiling-point compounds by means of the Claisen distillation apparatus. (Post-Treatment, Isolation, and Purification) The light brown suspension obtained after the reaction was cooled to 5 C. by using an ice-water bath and filtered by suction, and the obtained crystal was washed with methanol, water and methanol successively and dried by heating under reduced pressure to give 6.07 g of the title compound (1B-1) as a light yellow powder. Isolated yield: 76.6%. 1H NMR (400 MHz, CD2Cl2): δ=7.86-7.75 (m, 8H), 7.45-7.38 (m, 12H), 3.89 (br t, 1H), 3.53-3.36 (m, 2H), 3.05-2.95 (m, 2H), 2.62-2.44 (m, 4H), -15.2 (t, J=19.6 Hz, 1H). 31P NMR (161 MHz, CD2Cl2): δ=52.8 (d, J=6.0 Hz, 2P). A coordination isomer [δ=55.4 (d, J=6.1 Hz, 2P)] produced as a by-product in the conventional production method was not observed at all.
  • 46
  • [ 52462-29-0 ]
  • [ 2517-43-3 ]
  • [ 550373-32-5 ]
  • [ 1421060-11-8 ]
YieldReaction ConditionsOperation in experiment
77.8% Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 3-methoxy butanol; bis[2-(dicyclohexylphosphanyl)ethyl]amine for 1h; Inert atmosphere; Reflux; Stage #2: With sodium ethanolate for 1h; Inert atmosphere; Reflux; 4 A 50 mL four-necked round-bottomed flask equipped with a magnetic stirring bar, condenser, Claisen distillation apparatus, thermometer, and a three-way stopcock was evacuated and filled with nitrogen gas. Then, 3-methoxy-1-butanol (boiling point: 157° C., 20 mL), dichloro(p-cymene)ruthenium(II) dimer (2B-1) (1.0 g, 1.63 mmol, 1.0 equivalent), and bis[(2-dicyclohexylphosphino)ethyl]amine (3B-2) (1.59 g, 3.42 mmol, 2.1 equivalents) were charged into the flask successively. The obtained red suspension was stirred under reflux for 1 hour and then cooled to room temperature to obtain a crude product of dichloro{bis[2-(dicyclohexylphosphino)ethyl]amine}ruthenium(II) dimer (4B-2) as a red-orange suspension. NaOEt (249 mg, 3.59 mmol, 2.2 equivalents) was added to the suspension above, and the resulting suspension was stirred under reflux for 1 hour while distilling off low-boiling-point compounds by means of the Claisen distillation apparatus. (Post-Treatment, Isolation, and Purification) The light brown suspension obtained after the reaction was cooled to 5° C. by using an ice-water bath and filtered by suction, and the obtained crystal was washed with methanol, water and methanol successively and dried by heating under reduced pressure to give 1.60 g of the title compound (1B-2) as an off-white powder. Isolated yield: 77.8%. 1H NMR (400 MHz, CD2Cl2): δ=3.42 (t, J=12.0 Hz, 1H), 3.28-3.12 (m, 2H), 2.42-2.16 (m, 8H), 2.04-1.18 (m, 42H), -16.38 (t, J=18.4 Hz, 1H). 31P NMR (161 MHz, CD2Cl2): δ=65.2 (d, J=15.9 Hz, 2P).
  • 47
  • [ 2517-43-3 ]
  • [ 331861-94-0 ]
  • N,N′-bis(2,6-diisopropylphenyl)-1-bromo-7-(3-methoxybutoxy)perylene-3,4,9,10-tetracarboxylic diimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; 2.3.1. N,N′-Bis(2,6-diisopropylphenyl)-1-bromo-7-(3-methoxybutoxy)-perylene-3,4,9,10-tetracarboxylicdiimide (4a) 3 (1.00 g, 1.15 mmol), 3-methoxy-1-butanol (0.60 g, 5.76 mmol)and potassium carbonate (0.80 g, 5.76 mmol) in N,N-dimethylmethanamide(DMF) (60 ml) was stirred under nitrogen atmosphere for 3 h at80 °C. The reaction mixture was cooled to room temperature andpoured into 0.5M HCl (300 ml). The precipitate was filtered, repeatedlywashed with water, and dried in vacuum at 80 °C. The crude productwas purified by silica gel column chromatography with CH2Cl2 aseluent to obtain unreacted 3 (0.65 g, 65% yield) and desired 4a as redsolid compound (0.19 g, 19%). 1H NMR (CDCl3, 500 MHz): δ 9.66 (d,1H, J=12.8 Hz), 9.55 (d, 1H, J=13.6 Hz), 9.03 (s, 1H), 8.78 (d, 1H,J=13.6 Hz), 8,71 (d, 1H, J=12.8 Hz), 8.62 (s, 1H), 7.53-7.50 (m,2H), 7.38-7.36 (m, 4H), 4.70-4.64 (m, 2H), 3.72 (sextet, 1H), 3.39 (s,3H), 2.80 (septet, 4H), 2.25-2.73 (m, 2H), 1.32 (d, 4H, J=10.4 Hz),1.20-1.89 (m, 24H); 13C NMR (125 MHz, CDCl3): δ 163.61, 163.59,163.56, 162.97, 157.83, 145.86, 145.82, 138.56, 134.77, 134.22,133.42, 131.87, 130.62, 130.58, 130.09, 129.96, 129.83, 129.15,128.67, 128.54, 128.30, 124.37, 124.34, 123.33, 122.53, 121.65,120.75, 119.98, 118.85, 77.48, 77.22, 76.97, 73.83, 67.96, 56.46,36.75, 29.45, 24.23, 19.46; MALDI-TOF (m/z): calcd for [M+3H]3+:893.20. Found: 893.42; Elemental analysis: calcd for C53H51N2O6: C,71.37; H, 5.76; N, 3.14; O, 10.76. Found: C, 71.35; H, 5.90; N, 3.00; O,10.84.
  • 48
  • [ 625-38-7 ]
  • [ 2517-43-3 ]
  • 3-methoxy-1-butyl-3-butenoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With toluene-4-sulfonic acid In toluene at 130℃; for 4h; Dean-Stark; Inert atmosphere; 3 (Example 3)Synthesis of 3-methoxy-1-butyl-3-butenoate Vinylacetic acid synthesized in Example 1 (formula (1-0), 7.75 g, 90 mmol), 3-methoxy in a 100 mL two-necked flask equipped with a Dimroth reflux condenser, a Dean-Stark trap, and a nitrogen introduction tube -1-Butanol (9.37 g, 90 mmol), p-toluenesulfonic acid monohydrate (0.86 g, 4.5 mmol) and toluene (35 mL) were added. The two-necked flask was immersed in an oil bath, and the temperature of the oil bath was raised to 130 ° C. While maintaining the same temperature, the mixture was stirred for 4 hours under a nitrogen stream to distill off the by-produced water. The two-necked flask was cooled to room temperature (25 ° C.), washed three times with saturated aqueous sodium hydrogen carbonate (10 mL), further washed twice with distilled water (10 mL), and then dried over magnesium sulfate. After removing the magnesium sulfate, the solution was concentrated under reduced pressure. The resulting concentrated residue was distilled under reduced pressure in the same manner as in Example 2 to isolate compound (1-2a) (3-methoxy-1-butyl-3-butenoate) (12.33 g, yield 80%). The physical properties of the obtained compound (1-2a) are shown below.
  • 49
  • [ 1444-65-1 ]
  • [ 2517-43-3 ]
  • 3-methoxybutyl 6-oxo-6-phenylhexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With sulfuric acid; aurin; oxygen In toluene at 20℃; for 24h; Schlenk technique; Irradiation;
  • 50
  • [ 116-11-0 ]
  • [ 201230-82-2 ]
  • [ 2517-43-3 ]
YieldReaction ConditionsOperation in experiment
With dicobalt octacarbonyl; triisobutylphosphane; hydrogen; zinc dibromide In tert-butyl methyl ether at 150℃; for 4h; Glovebox; Autoclave; 1; 2; 3; 4; 5; 9; 10 Synthesis of 3-Methoxybutanol from 2-Methoxypropylene Catalyzed by Cobalt In the glove box,Add [Co(octanoate)2](0.35g,1.0mmol),P(iBu)3 (1.01g, 5.0mmol) and methyl tert-butyl ether (40.0g) were added to a single-necked flask equipped with a magnetic stir bar,Turn on the stirring,After the metal precursor and the ligand are dissolved and coordinated for 20 minutes,Get the catalyst solution,Seal the single-mouth bottle,Out of the glove box,Under the protection of nitrogen, use the advection pump to pump the catalyst solution into the autoclave that has been replaced with nitrogen in advance.Then add 2-methoxypropene (144.2g, 2.0mol),A solution of zinc bromide (0.45g, 2.0mmol) in methyl tert-butyl ether (30g), and finally a small amount of methyl tert-butyl ether (5g) is fed, and the residue in the feeding pipeline is washed into the reactor . After all the materials are added, replace the nitrogen with syngas three times, each 1.0MPa, and finally fill with 13.0MPa syngas (CO:H2=1:1), turn on the autoclave for stirring and jacket heating, when the temperature inside the reactor When it reaches 150°C, start timing and keep the reaction warm, and the synthesis gas is continuously introduced during the reaction process to keep the reaction pressure stable. After 4 hours of reaction, sampling and analysis showed that the conversion of 2-methoxypropene was 98.9%, the selectivity of the product 3-methoxybutanol was 96.1%, and the by-product was mainly 2-methoxypropane.
  • 51
  • [ 87-51-4 ]
  • [ 2517-43-3 ]
  • C15H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27.25 g With sulfuric acid In ethanol for 10h; Reflux; 9 Synthesis of photoacid generator (A4-4) Add 100.10g of 3-methoxybutanol and 20.01g of indole-3-acetic acid to a four-necked flask, then add dropwise 20.05g of sulfuric acid at room temperature, raise the temperature to 150°C, stir and react for 3h, then cool to room temperature, and wash with water three times. Take the organic layer and add dichloromethane and pure water, wash 2-3 times to neutrality, add 1.02 g of anhydrous sodium sulfate, suction filtration, and then distill under reduced pressure to obtain 27.25 g of solid.
  • 52
  • [ 2517-43-3 ]
  • [ 111-66-0 ]
  • [ 201230-82-2 ]
  • C14H28O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With manganese(I) pentacarbonyl bromide; water monomer; C34H24N3P; palladium (II) chloride In toluene at 120℃; for 20h; regioselective reaction;
Same Skeleton Products
Historical Records

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