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[ CAS No. 107-21-1 ] {[proInfo.proName]}

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Chemical Structure| 107-21-1
Chemical Structure| 107-21-1
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Quality Control of [ 107-21-1 ]

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Product Details of [ 107-21-1 ]

CAS No. :107-21-1 MDL No. :MFCD00002885
Formula : C2H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :62.07 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 107-21-1 ]

Physicochemical Properties

Num. heavy atoms : 4
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 14.05
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.7
Log Po/w (XLOGP3) : -1.36
Log Po/w (WLOGP) : -1.03
Log Po/w (MLOGP) : -1.15
Log Po/w (SILICOS-IT) : -0.64
Consensus Log Po/w : -0.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.7
Solubility : 310.0 mg/ml ; 4.99 mol/l
Class : Highly soluble
Log S (Ali) : 1.01
Solubility : 636.0 mg/ml ; 10.2 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.63
Solubility : 264.0 mg/ml ; 4.26 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 107-21-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P260-P264-P270-P301+P312+P330-P314-P501 UN#:N/A
Hazard Statements:H302-H373 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 107-21-1 ]

* 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 [ 107-21-1 ]

[ 107-21-1 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 22929-52-8 ]
  • [ 107-21-1 ]
  • [ 176-34-1 ]
YieldReaction ConditionsOperation in experiment
80% toluene-4-sulfonic acid; In benzene; for 17h;Heating / reflux; 1,4,7-Trioxaspiro[4.4]nonane. A mixture of intermediate 12 (15.79 g, 183.5 mmol), ethylene glycol (16.7 mL, 300 mmol) and cat. TsOH.H2O (100 mg) in benzene (100 mL) was heated at reflux using Dean-Stark trap. After 17 h, the reaction mixture was cooled, diluted with ether (150 mL), washed with sat. Na2CO3 and brine (50 mL each), dried (Na2SO4), filtered and concentrated to give yellow liquid. Distillation under reduced pressure afforded intermediate 13 as a yellow liquid (19.13 g, 80percent). 1H NMR (500 MHz, CDCl3) delta: 3.9.4 (2H, t, J=7.0 Hz), 3.94-3.90 (4H, m), 3.68 (2H, s), 2.09 (2H, t, J=7.0 Hz).
80% toluene-4-sulfonic acid; In benzene; for 17h;Heating / reflux; Intermediate 13l,4, 7~Trioxaspiro[4.4]nonane. A mixture of intermediate 12 (15.79 g, 183.5 mmol), ethylene glycol (16.7 mL, 300 mmol) and cat. TsOH*H2O (100 mg) in benzene (100 mL) was heated at reflux using Dean-Stark trap. After 17 h, the reaction mixture was cooled, diluted with ether (150 mL), washed with sat. Na2CO3 and brine (50 mL each), dried (Na2SO4), filtered and concentrated to give yellow liquid. Distillation under reduced pressure afforded intermediate 13 as a yellow liquid (19.13 g, 80percent). 1H NMR (500 MHz, CDCl3) delta: 3.9.4 (2H, t, J = 7.0 Hz), 3.94- 3.90 (4H, m), 3.68 (2H, s), 2.09 (2H, t, J = 7.0 Hz).
80% toluene-4-sulfonic acid; In benzene; for 17h;Heating / reflux; 1,4,7-Trioxaspiro[4.4]nonane. A mixture of ethyl 3'-hydroxy-4'-oxo-6',7'-dihydro-4'H-spiro[cyclopentane-1,9'-pyrimido[2,1-c][1,4]oxazine]-2'-carboxylate (15.79 g, 183.5 mmol), ethylene glycol (16.7 mL, 300 mmol) and cat. TsOH.H2O (100 mg) in benzene (100 mL) was heated at reflux using Dean-Stark trap. After 17 h, the reaction mixture was cooled, diluted with ether (150 mL), washed with sat. Na2CO3 and brine (50 mL each), dried (Na2SO4), filtered and concentrated to give yellow liquid. Distillation under reduced pressure afforded the title compound as a yellow liquid (19.13 g, 80percent). 1H NMR (500 MHz, CDCl3) delta: 3.9.4 (2H, t, J=7.0 Hz), 3.94-3.90 (4H, m), 3.68 (2H, s), 2.09 (2H, t, J=7.0 Hz).
  • 2
  • [ 31872-62-5 ]
  • [ 107-21-1 ]
  • 2-((3-nitropyridin-4-yl)oxy)ethanol [ No CAS ]
  • 3
  • [ 422-64-0 ]
  • [ 107-21-1 ]
  • [ 354-33-6 ]
  • 5
  • [ 3364-80-5 ]
  • [ 107-21-1 ]
  • [ 41029-82-7 ]
  • 6
  • [ 7716-66-7 ]
  • [ 107-21-1 ]
  • [ 21309-68-2 ]
  • 7
  • [ 7716-66-7 ]
  • [ 107-21-1 ]
  • [ 23514-47-8 ]
  • 8
  • [ 1454-85-9 ]
  • [ 107-21-1 ]
  • [ 24897-46-9 ]
  • 9
  • [ 107-21-1 ]
  • [ 112-26-5 ]
  • [ 5617-32-3 ]
  • 10
  • [ 646-06-0 ]
  • [ 50-00-0 ]
  • [ 5694-68-8 ]
  • [ 628-35-3 ]
  • [ 31144-13-5 ]
  • [ 39239-93-5 ]
  • [ 107-21-1 ]
  • [ 141-46-8 ]
  • 11
  • [ 5694-68-8 ]
  • [ 107-21-1 ]
  • 12
  • [ 201230-82-2 ]
  • [ 5694-68-8 ]
  • [ 71-23-8 ]
  • [ 64-17-5 ]
  • [ 107-21-1 ]
  • 13
  • [ 5731-01-1 ]
  • [ 107-21-1 ]
  • [ 107967-74-8 ]
  • 14
  • [ 5197-65-9 ]
  • [ 107-21-1 ]
  • [ 5617-32-3 ]
  • 15
  • [ 20357-21-5 ]
  • [ 107-21-1 ]
  • [ 135484-72-9 ]
  • 16
  • [ 107-21-1 ]
  • [ 646-06-0 ]
  • [ 497-26-7 ]
  • [ 5694-68-8 ]
  • [ 64-18-6 ]
  • [ 64-19-7 ]
  • 17
  • [ 106-93-4 ]
  • [ 108-59-8 ]
  • [ 75-21-8 ]
  • [ 6914-71-2 ]
  • [ 107-21-1 ]
  • 18
  • [ 391-12-8 ]
  • [ 107-21-1 ]
  • [ 113549-07-8 ]
  • 19
  • [ 119-60-8 ]
  • [ 107-21-1 ]
  • 2,2-Dicyclohexyl-[1,3]dioxolane [ No CAS ]
  • 20
  • [ 40473-07-2 ]
  • [ 107-21-1 ]
  • [ 17920-35-3 ]
  • 2-(6-methoxy-pyridin-2-yloxy)-ethanol [ No CAS ]
  • 21
  • [ 7089-68-1 ]
  • [ 107-21-1 ]
  • [ 546125-23-9 ]
  • 22
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • [ 126213-50-1 ]
YieldReaction ConditionsOperation in experiment
46.7% With toluene-4-sulfonic acid; In methanol; toluene; at 100℃; for 3h;Inert atmosphere; The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography.
  • 23
  • [ 51329-16-9 ]
  • [ 107-21-1 ]
  • [ 20197-75-5 ]
  • 24
  • [ 3032-81-3 ]
  • [ 107-21-1 ]
  • [ 115652-52-3 ]
  • [ 861648-82-0 ]
  • 2-(3,5-dichlorophenoxy)ethanol [ No CAS ]
  • 25
  • [ 107-21-1 ]
  • [ 148625-35-8 ]
  • [ 929897-33-6 ]
  • 26
  • [ 7469-77-4 ]
  • [ 107-21-1 ]
  • [ 869476-53-9 ]
YieldReaction ConditionsOperation in experiment
64.3% With [bis(acetoxy)iodo]benzene; at 20℃; for 4h; <strong>[7469-77-4]2-Methyl-1-naphthol</strong> [20] (5.0 g, 31.6 mmol) dissolved in ethylene glycol (100 mL) was added to a round bottomed flask (500 mL), containing iodobenzene diacetate (21.4g, 66.4 mmol) dissolved in ethylene glycol (100 mL) and stirred with a mechanical stirrer at RT for 4 hr. Reaction was quenched by addition of H2O (50 mL) followed by extraction with diethyl ether (3 x 150 mL). The organic phase was washed with saturated NaCI solution (2 x 200 mL), dried over anhydrous Na2SO4 and dried in vacuo. Flash chromatography using silica gel with 50percent ether in hexane yielded [21] (4.4 g, 64.3percent. FTIR (lambdamax cm-1) : 3290, 3074, 2984, 2910, 1658. 1H NMR (500 MHz, C6D6) : 1.84 (s, 3H, H-2), 3.55 - 3.67 (m, 4H, OCH2CH20), 6.29 (s, 1H, H-3), 7.01 (t, 1H, J=7.8 Hz, ArH-6), 7.15 (t, 1H, J=7.8 Hz, ArH-7), 7.48 (d, 1H, J=7.8 Hz, ArH-5) and 8.22 (dd, 1H, J=7.8,0.8 Hz, ArH-8). HRMS: Calculated for C13H12O3, 216.0786: Found: 216.0790.
  • 27
  • [ 10165-86-3 ]
  • [ 107-21-1 ]
  • [ 849662-01-7 ]
YieldReaction ConditionsOperation in experiment
81% toluene-4-sulfonic acid; In toluene; for 7.5h;Heating / reflux; 6-Formyl-nicotinic acid methyl ester (300 mg, 1.82 mmol) was dissolved in toluene (25 ml) and ethylene glycol (0.33 ml, 5.92 mmol) and p-toluenesulfonic acid (cat) were added. The mixture is refluxed with a dean-stark for 7.5 hours. The solvents are evaporated and the crude product was purified by column chromatography (SiO2, CH2Cl2/MeOH =99/1). The protected aldehyde was obtained as a white solid (310 mg, 81 percent). 1H NMR (400 MHz, CDCl3, 298K) delta 9.18 (d, 3J(H, H) = 1.8 Hz, 1H, ArH), 8.31 (dd, 3J(H, H) = 8.2Hz ; 2.2 Hz, 1H, ArH), 7.59 (d, 3J(H, H) = 8.0 Hz, 1H, ArH), 5.87 (s, 1H, CH), 4.16-4.05 (m, 4 H, CH2), 3.93 (s, 3 H, CH2). 13C NMR (100 MHz, CDCI3, 298K) delta 165.5 (C=O), 161.0 (ArC), 150.5 (ArCH), 138.0 (ArCH), 126.2 (ArC), 120.3 (ArCH), 103.1 (CH), 65.7 (CH2), 52.5 (CH3).
  • 28
  • [ 504-24-5 ]
  • [ 107-21-1 ]
  • [ 253-72-5 ]
YieldReaction ConditionsOperation in experiment
36% With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 135℃; for 4h; A sulfuric acid solution was prepared by adding H2SO4 (100 mL) to H2O (57 mL) cooled in an ice bath. To this solution was added glycerol (33 mL, 457 mmol),m-nitrobenzene sulfonic acid sodium salt (48 g, 212 mmol) and 4-amino-pyridine (10 g, 106 mmol). The reaction mixture was heated at 135°C for 4 hours. The cooled reaction mixture was basicified with 2.5 N NaOH (500 mL) with cooling in an ice bath, and extracted into CH2Cl2 (3 x 200 mL). The organic fractions were combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (5percent MeOH/CH2Cl2) affording 5.04 g (36percent) as a dark orange oil. An analytical sample was prepared as the HCl salt from EtOAc yielding an orange low melting solid. MS EI m/z 130 M+. Ref: Chem Pharm Bull. 1971, 19, 9, p. 1751-1755
  • 29
  • [ 50690-11-4 ]
  • [ 107-21-1 ]
  • [ 13612-34-5 ]
  • 30
  • [ 3939-01-3 ]
  • [ 107-21-1 ]
  • [ 64996-14-1 ]
YieldReaction ConditionsOperation in experiment
A mixture of 20.0 gm (70.4 mMol) <strong>[3939-01-3]1-benzyl-3-methoxycarbonyl-4-oxopiperidine hydrochloride</strong> in 60 mL ethylene glycol was cooled in an ice bath as 24 gm hydrogen chloride were added. The slurry was heated at 70°C for 2 hours and was then poured into 200 mL ice water. The pH was adjusted to about 8 with 5N sodium hydroxide and the resulting mixture extracted well with diethyl ether. The organic extracts were combined, dried over sodium sulfate, and concentrated under reduced pressure to provide 21 gm 8-benzyl-8-azaspiro[4,5]decane-6-carboxylic acid methyl ester.
  • 31
  • [ 107-21-1 ]
  • [ 107-06-2 ]
  • [ 108-59-8 ]
  • [ 6914-71-2 ]
YieldReaction ConditionsOperation in experiment
With tetrabutylammomium bromide; potassium carbonate; EXAMPLE 4 Dimethyl 1,1-cyclopropanedicarboxylate 319.6 g of 1,2-dichloroethane (3.23 mol), 5 g of polyethylene glycol (mean molar mass 600 g/mol) and 168.0 g of potassium carbonate (1.2 mol) were initially introduced, and the reaction mixture was heated until the 1,2-dichloroethane refluxes. 132.1 g of dimethyl malonate (1 mol) and 1.25 g of tetrabutylammonium bromide (3.88 mmol) were then added at the boil. The mixture was stirred using a paddle stirrer for 6 hours. Water formed during the reaction was removed by azeotropic distillation with 1,2-dichloroethane throughout the reaction.
  • 32
  • [ 2001-29-8 ]
  • [ 107-21-1 ]
  • [ 107028-36-4 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; for 15h;Heating / reflux; A solution of l-(4-bromophenyl)-2-phenylethanone (5.0 g, 18 mmol), ethylene glycol (3.0 mL, 54 mmol) and tosic acid (0.04 g, 0.2 mmol) in toluene (30 mL) was heated to reflux with a Dean-Stark trap for 15 hours. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to give crude 2-benzyl-2-(4-bromophenyl)-l,3-dioxolane as a white solid. To the crude material was added zinc cyanide (2.3 g, 20 mmol), tetrakis(triphenylphosphine)palladium (3.3 g, 2.8 mmol), DMF (20 mL) and dioxane (20 mL) and the resulting suspension was purged with nitrogen for 15 minutes prior to being heated 1000C for 15 hours. The reaction was cooled to room temperature, poured into ether and filtered. The organic filtrate was washed with water, saturated bicarbonate, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (1percent ethyl acetate/ hexane -> 50percent ethyl acetate/ hexane) gave the title compound as white solid. MS (M+H"1"): calculated = 265.31, observed = 266.1
  • 33
  • [ 68500-37-8 ]
  • [ 107-21-1 ]
  • [ 1051315-78-6 ]
  • C22H20N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example IA <n="52"/>5-Bromo- l-(2-(7-methoxy quinolin-4-yloxy)ethyl)py ridin-2 (1 H)-one; Alternative synthesis of 5-Bromo- l-(2-(7-methoxyquinolin-4- yloxy)ethyl)pyridin-2( 1 H)-one2-(7-Methoxyquinolin-4-yloxy)ethanol. In a IL RBF under nitrogen was placed sodium (15 g, 652 mmol) cubes. The flask was cooled in an ice bath and ethane- 1,2-diol (150 ml, 2690 mmol) was added slowly through an addition funnel (15min). The cooling bath was removed and the reaction mixture was allowed to warm to ~ 50 0C until all the sodium disappeared. After 20 min, the mixture was heated to 110 0C and <strong>[68500-37-8]4-chloro-7-methoxyquinoline</strong> (69 g, 356 mmol) was added. After 12 h, the mixture was cooled to room temperature and was diluted with H2O (250 mL), resulting the formation of a thick sludge. The content was filtered, and washed with H2O (2x50 mL). After air drying overnight, the solid was heated with benzene (300 mL) under reflux for 3 hr. The mixture was cooled and filtered. The solid was washed with ether (2 x 50 mL) to give a soft solid (77 g) contaminated with the small amount of bisether dimer. MS (ESI pos. ion) calcd for Ci2H13NO3: 219.2; found: 220.1 (MH+). 1H NMR (400 MHz, Chloroform-d) delta ppm 3.94 (s, 3 H) 4.13 (t, 2 H) 4.32 (t, 2 H) 6.64 (d, J=5.28 Hz, 1 <n="53"/>H) 7.14 (dd, J=9.19, 2.54 Hz, 1 H) 7.37 (d, J=2.35 Hz, 1 H) 8.08 (d, J=9.19 Hz, 1 H) 8.66 (d, J=5.48 Hz, 1 H)
  • 35
  • [ 107-21-1 ]
  • [ 141-46-8 ]
  • [ 5694-68-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 20℃; for 1h; In a four necked round-bottomed glass reactor, equipped with magnetic stirrer, thermometer, condenser maintained at -75°C (dry ice-lsopropyl alcohol) and two addition funnels, 60 g of glycol aldehyde (1.0 mol) and 62 g of ethylene glycol (1.0 mol) were loaded, followed by 10 g of 37percent HCI water solution (0.10 mol HCI) at room temperature; after 1 hour under stirring, the formation of cyclic acetal (G) was complete; the reactor was thus cooled to 0°C with an ice water bath, then a solution of 44 g (1.1 mol) of NaOH (s) and 44 ml of distilled water H2O was added in half an hour. After a slight exothermicity, at 0°C, 216 g (1.0 mmol) of (A) were slowly added. At the end of the addition, the reaction mixture was allowed to reach 20°C, and stirred for another 2 hours. The crude mixture was extracted three times with tetrahydrofuran (THF). The combined THF extracts were dehydrated with MgSO4, filtered and fractionally distilled, collecting 247 g of the partially hydrogenated ether (H) (yield 77percent mol). The aldehyde group of adduct (H) was deprotected (quantitatively) obtaining the corresponding aldehyde (J) by hydrolysis in acidic conditions (diluted HCI).
  • 37
  • [ 6342-79-6 ]
  • [ 622-40-2 ]
  • [ 51068-78-1 ]
  • [ 107-21-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;Cu/Al2O3/SiO2; In methanol; at 170℃; under 41254.1 Torr; for 16.5h;Autoclave; HydrogenationThe hydrogenation experiments were performed in a multi-autoclave unit containing four 60 ml batch autoclaves, all equipped with common electrical heating and with individual gas entrainment impellers, manometers and temperature indication . The hydrogenation catalysts were activated in-situ (typical conditions : 230 0C, 10 - 20 bar H2 for 4 hrs ) . The substrates, dissolved in ca . 20 ml solvent , were introduced into the autoclaves by injection. Then, the autoclaves were pressurized with Hz, stirred at 800 rpm and heated to ca. 170 0C. After the reaction, the liquid reactor contents were analyzed by GC-MS. Table 2 shows the reaction conditions and analytical results from the different experiments. Table 23 This specie was qualitatively observed by NMR analysis and/or GC-MS.4 GC-MS peak area percentage (Anpercent) = (peak area n) x 100 / (sum of substrate, 2-hydroxyacetamide, MEG, HOCH2CH2NR2, R2NCH2CH2NR2 and all polyamine peak areas) .5 MEG peak corrected for overlaying methyl glycolate peak (10percent peak area reduction) . n.d. = not determined
  • 38
  • [ 6292-59-7 ]
  • [ 107-21-1 ]
  • [ 150728-13-5 ]
  • [ 147536-97-8 ]
  • 39
  • 4,6-dichloro-5-(2-methoxybenzyl)-2,2-bipyrimidine [ No CAS ]
  • [ 6292-59-7 ]
  • [ 107-21-1 ]
  • [ 147536-97-8 ]
YieldReaction ConditionsOperation in experiment
Example 1PREPAPARATION OF AMMONIUM SALT OF BOSENTANTo a stirred solution of 4,6 dichloro-5-(2-methoxybenzyl)-2,2-bipyrimidine (100 gm) in acetonitrile (1000ml), <strong>[6292-59-7]4-tert-butylbenzenesulphonamide</strong> (67.16 gm) and potassium carbonate (340 gm) were added with stirring at 25°C to 30 °C. The reaction mass was stirred at 80°C to 85° C for 2 to 4 hours. After completion of the reaction which was monitored by TLC, ethylene glycol (1000 ml) was added to the reaction mass and the resulting reaction mixture was further stirred at 80°C to 85°C for 25to 30 hours. After completion of the reaction (by HPLC), the reaction solution was cooled at 25°C to 30°C and it was diluted with water (1000 ml). The pH of the solution was adjusted to pH 4.0 to 5.0 using concentrated hydrochloric acid.The resulting reaction solution was extracted with diehloromethane (1000 ml). The dichloromethane layer was washed with 5percent brine solution (2x1000 ml) and distilled off completely to obtain the residue. The residue was suspended with 3: 1 mixture of isopropyl acetate (780 ml), ethanol (260 ml) followed by ammonium hydroxide (158 ml) and the resulting mixture was heated at 50°C to 55°C for 30 minutes. The mixture was cooled to 5°C -10°C and it was maintained for 5 to 6 hours. The solid obtained was filtered and dried to obtain the ammonium salt of Bosentan 145.0 gm [86.4percent]. The salt is characterized by melting point, IR, NMR and elemental analysis. Melting Point: 172-174°C;IR having characteristic peaks at 580, 1136, 1251 , 1558, 2965, 3277 cm"1 ;The NMR, 1H NMR (DMSO) of ammonium salt of Bosentan of the formula (VIII) having characteristic peaks at delta 8.97-8.98 (d, 2H), 7.97-7.99(d, 2H), 7.55-7.58 (t, 1H), 7.25-7.27 (d, 2H), 7.00-7.02 (d,lH) 6.86-6.90) (t, 1H) 6.70-6.74 (t,lH) 6.35-6.37 (d ,1H) 4.86-4.89 (t ,lH),4.22-4.25(t, 2H) 3.83 (s, 3H) 3.51-3.52(q,2H)1.23(s,9H) as demonstrated in figure 5.Elemental analysis for C27H32N606S: Theoretical (percent) C: 56.98; H: 5.10; N: 14.77.Found (percent) C: 56.67; H : 5.50; N: 14.78.The novel crystalline form of ammonium salt of Bosentan is characterized by its XPRD pattern having characteristic peaks at 5.96, 6.79, 9.09, 9.26, 10.52, 16.64, 17.60, 18.14, 18.53, 22.49, 24.29, 24.91 , and 27.5 +/- 0.2 degrees 2Psi and its XRPD pattern is as per Figure 1
  • 40
  • [ 80041-89-0 ]
  • [ 107-21-1 ]
  • 2-(propan-2-yl)-1,3,2-dioxaborolane [ No CAS ]
  • 42
  • [ 6292-59-7 ]
  • [ 107-21-1 ]
  • [ 150728-13-5 ]
  • 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide potassium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step-A: Preparation of 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide potassium salt (bosentan potassium salt (VI)) 4,6 dichloro-5-(2-methoxybenzyl)-2,2-bipyrimidine (II) (50 g, 0.143 moles) and anisole (750 ml) were placed in a reaction flask. Potassium carbonate (118.4 g, 0.858 moles) was added and reaction mass was stirred for 15 minutes. <strong>[6292-59-7]4-tert-butylbenzenesulphonamide</strong> (III) (30.5 g, 0.143 moles) was added to reaction mass and heated to 120° C. for 7 hours. Ethylene glycol (1.110 g, 17.9 moles) was charged to reaction mass and maintained at 120° C. for 5 hours and brought to room temperature. Reaction mass was poured into purified water (4.5 L) and stirred for 30 minutes. The precipitated solid was isolated by filtration and washing with acetonitrile to afford bosentan potassium salt.(83 g, yield 90percent, purity by HPLC: 91.2percent with 0.159percent impurity-A, 0.686percent impurity-B and 7.8percent <strong>[6292-59-7]4-tert-butylbenzenesulphonamide</strong> (III))
  • 43
  • [ 553-26-4 ]
  • [ 569-51-7 ]
  • NO3(1-)*Cd(2+)*4H2O [ No CAS ]
  • [ 7732-18-5 ]
  • [ 107-21-1 ]
  • [Cd(1,2,3-benzene tricarboxyliate 2-(2-hydroxy-ethyl) ester)(4,4'-bipyridine)(H2O)]·0.5glycol·H2O}n [ No CAS ]
  • 44
  • [ 553-26-4 ]
  • [ 569-51-7 ]
  • NO3(1-)*Cd(2+)*4H2O [ No CAS ]
  • [ 7732-18-5 ]
  • [ 107-21-1 ]
  • [Cd6(1,2,3-benzenetricarboxyliate)4(4,4′-bipyridine)4.5(glycol)]·9H2O}n [ No CAS ]
  • 45
  • [ 4903-09-7 ]
  • [ 107-21-1 ]
  • [ 773094-35-2 ]
YieldReaction ConditionsOperation in experiment
93% With toluene-4-sulfonic acid; In toluene; for 12h;Reflux; Dean-Stark; A solution of <strong>[4903-09-7]3-chloro-4-methoxybenzaldehyde</strong> (10c, 11.72 g, 0.068 mol), ethylene glycol (7.56 mL, 8.39 g, 0.135 mol) and p-toluenesulfonic acid (0.23 g, 1.3 mmol) in toluene (70 mL) was refluxed in a Dean-Stark apparatus for 12 h. The reaction mixture was washed with aqueous sodium hydrogen carbonate solution (5 w/wpercent, 100 mL) and water (2 x 100 mL), dried over MgSO4 and the solvent was evaporated to give 11c (13.60 g, 93percent) as a pale yellow oil. 1H NMR (DMSO-d6, 500 MHz) delta 7.48 (1H, d, J=2.1 Hz), 7.38 (1H, dd, J=8.4, 2.1 Hz), 7.13 (1H, d, J=8.4 Hz), 5.69 (1H, s), 4.05 (2H, m), 3.93 (2H, m), 3.87 (3H, s). 13C NMR (DMSO-d6, 100 MHz) delta 155.3, 131.6, 128.1, 126.9, 121.1, 122.5, 102.1, 64.9, 56.2. IR (KBr, cm-1) 2890, 1507, 1265. Anal. Calcd for C10H11ClO3 (214.65): C 55.96, H 5.17, Cl 16.52percent. Found: C 55.56, H 5.23, Cl 16.40percent.
  • 46
  • [ 6638-05-7 ]
  • [ 107-21-1 ]
  • [ 1574215-65-8 ]
  • [ 1574215-63-6 ]
  • 47
  • [ 6638-05-7 ]
  • [ 107-21-1 ]
  • [ 1574215-63-6 ]
  • [ 134-96-3 ]
YieldReaction ConditionsOperation in experiment
26%; 65% With oxygen; cobalt(II) acetate; sodium hydroxide; In water; at 50℃; under 760.051 Torr; for 3.0h;Green chemistry;Mechanism; General procedure: Procedure for Scheme 2(a): mixture of substrate 1 (5.0 mmol), Co(OAc)2*4H2O (0.05 mmol, 12 mg)and NaOH (5.0 mmol, 0.2 g) in EG/H2O (5.0 mL/0.25 mL) was stirred with O2 (1.0 atm) being bubbled at 50 °C for 3 h. Hydrochloric acid (10.0 mL, 2 percent) and chloroform (10.0 mL) were successively added to reaction mixture. The chloroform phase was separated, and the aqueous phase was further extracted with chloroform (10.0 mL × 2). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography on silica gel (eluents:petroleum ether/ethyl acetate, 5/1) to provide the intermediates 3 and desired products 2.
  • 48
  • [ 6638-05-7 ]
  • [ 107-21-1 ]
  • [ 1574215-63-6 ]
  • 49
  • [ 84405-44-7 ]
  • [ 107-21-1 ]
  • C18H14Br2O4 [ No CAS ]
  • 50
  • [ 107-21-1 ]
  • [ 119389-05-8 ]
  • [ 1398110-00-3 ]
  • 51
  • [ 43192-34-3 ]
  • [ 107-21-1 ]
  • 2-(4-bromo-3-methoxyphenyl)-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With toluene-4-sulfonic acid; In toluene; for 4h;Reflux; To a solution of <strong>[43192-34-3]4-bromo-3-methoxybenzaldehyde</strong> (0.56 g, 2.6 mmol) obtained above in toluene (25 mL) was added para-toluenesulfonic acid (p- TsOH) (0.02 g, 0.1 mmol) And ethylene glycol (5 mL, 89.4 mmol). The mixture was heated at reflux for 4 hours, then cooled and diluted with ethyl acetate (25 mL). The mixture is washed with saturated aqueous sodium hydrogencarbonate solution, and then magnesium sulfate is added to remove moisture, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ether = 8: 1) to give 2- (4-bromo-3-methoxyphenyl) Bromo-3-methoxyphenyl) -1,3-dioxolane in the form of a colorless oil(76percent yield)
  • 52
  • [ 55589-47-4 ]
  • [ 107-21-1 ]
  • 2-(1,3-dioxolan-2-yl)-3-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.63 g In toluene;Reflux; Dean-Stark; A mixtureof 3-methylpicolinaldehyde (2.0 g, 16.5 mmol), ethylene glycol(10 mL), and p-toluenesulfonic acid monohydrate (50 mg) in toluene (15 mL) was heated at reflux with Dean?Stark apparatus overnight. The mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (EtOAc) toyield 9 (2.63 g, 97percent) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 8.46 (1H, dd, J=4.6, 1.0 Hz),7.48 (1H, dd, J=8.0, 0.8 Hz), 7.19 (1H, dd, J=8.0, 4.6 Hz), 6.00(1H, s), 4.23?4.27 (2H, m), 4.06?4.10 (2H, m), 2.44 (3H, s).MS (ESI) m/z: 166.1 (M+H)+. HPLC purity 98.3percent (1.98 min,method B).
  • 53
  • [ 1570-05-4 ]
  • [ 107-21-1 ]
  • 2-hydroxyethyl 3,4-bis(benzyloxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; at 80℃; Preparation of 2-hydroxyethyl 3,4-bis(benzyloxy)benzoate (0176) 3,4-Bis(benzyloxy)benzoic acid was dispersed in ethylene glycol, and heated to 80° C. A catalytic amount of KOH was added to the solution that was left to react until all solids were dissolved. The solution was precipitated into cold water and left to stir for several hours, yielding a white solid. The solid was obtained by filtration, rinsed with water, and then freeze dried.
  • 54
  • [ 107-21-1 ]
  • [ 50607-30-2 ]
  • 1,4-dioxy-8-azaspiro[4.5]heptan-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.8% With toluene-4-sulfonic acid; In toluene; at 110℃; [0090] 2, 4- piperidinedione (300mg, 2.65mmol) was suspended in 25ml of toluene. Ethylene glycol (329mg, 5.3mmol)and p-toluenesulfonic acid monohydrate (100mg, 0.53mmol) were added, and water was removed from the resultingmixture by reflux at 110°C. TLC (DCM/MeOH=10/1) was employed to monitor the reaction. After the reaction completed,aqueous solution of sodium bicarbonate was added, and the resulting mixture was extracted with EA (30ml34). Theorganic phase was combined, washed with water and saturated saline solution for two times respectively, dried overanhydrous sodium sulfate, filtered, and the solvent was evaporated. Column chromatography (DCM/MeOH=50/1) affordedwhite solid 220mg, yield: 52.8percent.[0091] 1H NMR (300 MHz, CDCl3) delta 6.88-6.57 (s, 1H), 4.07-3.79 (dt, J = 6.4,3.1 Hz, 4H),3.46-3.25 (t, J = 6.2 Hz, 2H),2.67-2.52 (s, 2H), 1.96-1.81 (t, J = 6.1 Hz, 2H). MS(ESI) m/z :[(M+23)+,180.2].
  • 55
  • [ 90905-31-0 ]
  • [ 107-21-1 ]
  • 2-(methylthio)pyrimidine-5-carbaldehyde ethylene acetal [ No CAS ]
  • 56
  • [ 935-99-9 ]
  • [ 107-21-1 ]
  • 2-(2-bromo-5-chlorophenyl)-2-methyl-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% (a) 2-(2-Bromo-5-chlorophenyl)-2-methyl-1,3-dioxolane 1-(2-Bromo-5-chlorophenyl)ethanone (8.29 g, 35.50 mmol) was dissolved in toluene (180 mL) in a round-bottomed flask fitted with a Dean-Stark trap. Ethane-1,2-diol (5.96 mL, 106.51 mmol) and 4-methylbenzenesulfonic acid (0.67 g, 3.91 mmol) were added and the reaction mixture was heated at reflux for 3.5 h. The reaction mixture was cooled to r.t., an aq solution of K2CO3 (1 M) was added and the layers were separated. The aq phase was extracted with toluene and the combined organic layers were washed with water and with brine. The solution was dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 9.29 g (94percent) of the title compound. 1H NMR (500 MHz, CDCl3): delta 1.80 (s, 3H), 3.78 (m, 2H), 4.08 (m, 2H), 7.13 (m, 1H), 7.52 (m, 1H), 7.66 (m, 1H).
  • 57
  • [ 69976-81-4 ]
  • [ 107-21-1 ]
  • 2-methyl-3-(2-methyl-1,3-dioxolan-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.1% In toluene; for 3.5h;Inert atmosphere; Reflux; <strong>[69976-81-4]1-(3-hydroxy-2-methylphenyl)ethanone</strong> 13a (3 g, 20 mmol, prepared by a well known method disclosed in "Journal of Medicinal Chemistry, 52 (20), 6433-6446; 2009") and 30 mL of ethylene glycol were dissolved in 30 mL of toluene. After stirring for 3.5 hours under reflux, the reaction solution was added with 200 mL of ethyl acetate, washed with water (100 mL × 3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with eluent system B to obtain the title compound 2-methyl-3-(2-methyl-1,3-dioxolan-2-yl)phenol 13b (1.03 g, white solid), yield: 54.1%. MS m/z (ESI): 195.1 [M+1]
  • 58
  • [ 5731-01-1 ]
  • [ 107-21-1 ]
  • 2-bromomethyl-2-[4-(4-bromophenyl)phenyl]-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With pol(vinylphenyltrimethylammoniumtribromide) resin; at 45℃; for 24h; General procedure: A mixture of 2.5 mmol of substrate, and 5 mL ethylene glycol was tirred for 5 min, and then 1.1 g of PVBMATB resin was added, and the mixture was stirred 24 h at room temperature or 45C. Afterward, the resin of poly(vinylbenzyltrimethylammonium bromide) was recycled through filtration and washed with ether. The combined organic layer was washed twice by water (20 mL), and dried over anhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure, and the residual was treated with alumina chromatography (Petroleum ether/AcOEt = 20/1,v/v) to generate the product.
92% With N-Bromosuccinimide; at 20℃; for 24h; General procedure: A mixture of 2 mmol of substrate, and 6 mL ethylene glycol was stirred for 5 min, and then 4.6 mmol of NBS or 8 mmol of NCS was added by 5 times in one hour, and the mixture was stirred 24 h at room temperature or 45 C. After ward, the mixture was extracted with ether (10 mL3). The combined organic layer was washed twice by water (20 mL), and dried over anhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure, and the residual was treated with alumina chromatography (Petroleumether/AcOEt20/1,v/v) to generate the product.
  • 59
  • [ 688-74-4 ]
  • [ 107-21-1 ]
  • [ 171408-84-7 ]
  • C29H22B2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Under nitrogen protection and dry ice - acetone bath conditions,A 1.6 mol / L n-butyllithium / hexane solution (29 mL, 0.046 mol, 2.2 eq) was added dropwise to a solution of 2,(10 g, 0.021 mol, 1 eq) in tetrahydrofuran (200 mL) at -78 & lt; 0 & gt;The reaction was maintained at low temperature for 2 h;Tri-n-butyl borate (14.5 g, 0.063 mol, 3 eq) was maintained at low temperature for 0.5 h,Then, the reaction was carried out at room temperature for 10 h.2 mol / L hydrochloric acid (150 mL) was added,The reaction was terminated after 2 h. Extracted with methylene chloride,The organic phases were combined and dried over anhydrous magnesium sulphate,Concentrated in vacuo, dissolved in toluene (30 mL)Ethylene glycol (2.73 g, 0.044 mol, 2.1 eq) was added,Reaction at 110 ° C for 5 h,The reaction was stopped and allowed to stand,cool down,A white solid precipitated,The product was filtered off by suction,Yield 80.0percent.
  • 60
  • [ 1532-71-4 ]
  • [ 107-21-1 ]
  • 2-(isoquinolin-1-yloxy)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; copper dichloride; at 20 - 130℃; for 16h;Inert atmosphere; Sealed tube; General procedure: In a sealed tube, N-heteroaryl bromide 5a,c?k (10 mmol), CuCl2 (0.5 mmol) and K2CO3 (30 mmol) were charged and suspended in ethylene glycol (5 mL) and stirred at room temperature for 10 min. The blue colored suspension was refluxed at 130 °C for 16 h. The mixture was cooled to room temperature and diluted with H2O (10 mL) and extracted with ethyl acetate (3 × 30 mL). The combined organic layers were washed with Brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude residue was performed by column chromatography on silica gel (except for compound 6g, which was crystallized using dioxane/cyclohexane).
  • 61
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • C7H10O3S [ No CAS ]
  • C8H12O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
17.23%Chromat.; 5.38%Chromat. With 2-aminonaphthalenesulfonic acid; In methanol; toluene; at 100℃; for 1h;Inert atmosphere; General procedure: The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography. Except that 2-amino-1-naphthalenesulfonic acid monohydrate of the same substance (mol number) was used instead of the cuedemen sulphonic acid monohydrate of Example 5, and the compositional change in the reaction solution was evaluated by N, N-dimethylformamide was traced by gas chromatography as an internal standard. The relationship between the time from the start of reflux of toluene and the concentration of each component is summarized in Table 8.
  • 62
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • C7H10O3S [ No CAS ]
  • C8H12O4S [ No CAS ]
  • [ 126213-50-1 ]
YieldReaction ConditionsOperation in experiment
19.3%Chromat.; 12.84%Chromat.; 56.29%Chromat. With (+)-(1S)-camphor-10-sulphonic acid; In methanol; toluene; at 100℃; for 1h;Inert atmosphere; General procedure: The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography. ((+) - 10-camphistsulfonic acid monohydrate of the same substance amount (mol number) was used in place of the cuedemen sulphonic acid monohydrate of Example 5, the compositional change in the reaction solution was evaluated by N, N-dimethylformamide was traced by gas chromatography as an internal standard. Table 7 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.
7.3%Chromat.; 11.78%Chromat.; 70.74%Chromat. With 2-aminonaphthalenesulfonic acid; In methanol; toluene; at 100℃; for 3h;Inert atmosphere; General procedure: The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography. Except that 2-amino-1-naphthalenesulfonic acid monohydrate of the same substance (mol number) was used instead of the cuedemen sulphonic acid monohydrate of Example 5, and the compositional change in the reaction solution was evaluated by N, N-dimethylformamide was traced by gas chromatography as an internal standard. The relationship between the time from the start of reflux of toluene and the concentration of each component is summarized in Table 8.
  • 63
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • C7H10O3S [ No CAS ]
  • [ 126213-50-1 ]
YieldReaction ConditionsOperation in experiment
13.67%Chromat.; 79.08%Chromat. With para-dodecylbenzenesulfonic acid; In methanol; toluene; at 100℃; for 1h;Inert atmosphere; The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography. The same procedure as in Example 5 was repeated except that dodecylbenzene sulfonic acid monohydrate (moles) was used in place of the cuedemen sulphonic acid monohydrate in Example 5 to change the composition in the reaction solution to N, N-dimethylform The amide was traced by gas chromatography as an internal standard. The relationship between the time from the start of reflux of toluene and the concentration of each component is summarized in Table 5
  • 64
  • [ 51792-34-8 ]
  • [ 107-21-1 ]
  • C8H12O4S [ No CAS ]
  • [ 126213-50-1 ]
YieldReaction ConditionsOperation in experiment
14.42%Chromat.; 78.58%Chromat. With naphthalene-2-sulfonate; In methanol; toluene; at 100℃; for 3h;Inert atmosphere; The following production was carried out using <strong>[51792-34-8]3,4-dimethoxythiophene</strong> prepared by the same production method as in Example 2 described above. This also applies to Examples 5 to 9 and Comparative Examples 3 to 9 described below.First, 10.1 g of <strong>[51792-34-8]3,4-dimethoxythiophene</strong>, 6.74 g of ethylene glycol, 1.1 g of p-toluenesulfonic acid monohydrate and 76.6 g of toluene were placed in a 100 ml four-necked flask, and the mixture was heated and stirred in an argon atmosphere.And heated to 100 DEG C while distilling methanol at 95 deg. At 100 , the methanol flow terminated and toluene reflux started.The compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. As a result, <strong>[51792-34-8]3,4-dimethoxythiophene</strong> was found to be below the detection limit at the reflux time of 3 hours. Table 1 summarizes the relationship between the time from the start of reflux of toluene and the concentration of each component.The EDOT, DMEOT, mono- and di-substituents in Table 1 are3,4-ethylenedioxythiophene,<strong>[51792-34-8]3,4-dimethoxythiophene</strong>,One in which one methoxy group of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> is substituted with ethylene glycol,And methoxy groups of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> were replaced with ethylene glycol The conversion (percent) in the table is theoretically 3, 4-ethylenedioxythiophene when N, N-dimethoxyformamide is measured by gas chromatography as an internal standard, Represents the ratio of the amount of 4-ethylenedioxythiophene.The residual ratio (percent) likewise represents the ratio of the actual amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in the reaction solution to the amount of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> in theory.The reaction mixture was diluted with water, the insoluble material was removed by filtration, the crude product was extracted from toluene, the toluene layer was washed with water, washed with aqueous sodium hydrogencarbonate solution, and then dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated on a rotary evaporator to obtain a crude product.The yield of the crude product was 6.78 g (68.1percent) and the purity was 98.69percent by gas chromatography.The crude product was subjected to vacuum distillation to obtain 4.65 g (yield: 46.7percent) of 3,4-ethylenedioxythiophene. The purity of its 3,4-ethylenedioxythiophene was 99.64percent by gas chromatography. (Number of moles) of cadmium sulfonic acid monohydrate of Example 52-naphthalene sulfonic acidMonohydrate was used, and the compositional change in the reaction solution was followed by gas chromatography using N, N-dimethylformamide as an internal standard. The relationship between the time from the start of reflux of toluene and the concentration of each component is summarized in Table 5
  • 65
  • [ 6292-59-7 ]
  • [ 107-21-1 ]
  • [ 150728-13-5 ]
  • C27H28N5O6S(1-)*H4N(1+) [ No CAS ]
  • 66
  • [ 1953-99-7 ]
  • [ 107-21-1 ]
  • dichloro-2,3-dihydrobenzo-[1,4]dioxin-6,7-dicarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; calcium carbonate; In acetone; at 20℃; 3,4,5,6-<strong>[1953-99-7]tetrachlorophthalonitrile</strong> of 6 g (3 eq), KF of 1.8 g (3.1 eq), CaCO3 of 0.5 g (0.5 eq) and 1,2 ethanol of 2.5 g (4 eq) are put in acetone of about 30 ml to about 50 ml (30 eq), and reaction proceeds at room temperature overnight. When the completion of the reaction is verified by thin later chromatography (TLC), work-up is carried out. Subsequently, a resultant product is separated and purified by column chromatography.
  • 67
  • [ 1570-05-4 ]
  • [ 107-21-1 ]
  • ethane-1,2-diyl bis(3,4-bis(benzyloxy)-5-bromobenzoate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.0% General procedure: The intermediate 3a-d (1.0 mmol) was dissolved in dichloromethane (10.0 mL), which has been dried through refluxing, under nitrogen atmosphere. Then, DMAP (1.5 mmol), EDCI (1.25mmol) were added to it in order. Then, ethylene glycol (0.5 mmol), glycerin (0.3 mmol), ribose (0.25 mmol) or xylose (0.25 mmol) was added. After stirring for 24 h at room temperature, the mixture was poured into water and washed with 1 mol/L HCl. The CH2Cl2 layer was concentrated, and the residue was purified using flash chromatography (ethyl acetate: Petroleum ether, 1:100-1:20) to obtain 4-6a, 4-7c or 4-7d. Compound 6-7a, 4-7b, 6d were used directly in the next step without purification and structural characterization.
  • 68
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 107-21-1 ]
  • [ 5077-67-8 ]
  • [ 116-09-6 ]
  • [ 584-03-2 ]
  • 69
  • [ 9004-34-6 ]
  • [ 107-21-1 ]
  • [ 5077-67-8 ]
  • [ 116-09-6 ]
  • 70
  • [ 456-24-6 ]
  • [ 107-21-1 ]
  • [ 143071-39-0 ]
YieldReaction ConditionsOperation in experiment
91% Ethylene glycol (0.883 mL, 15.84 mmol) was dissolved in DMF (10 mL) at 0 °C. Sodium hydride (253 mg, 6.33 mmol, 60percent in mineral oil) was added to the reactionmixture portion wise and the reaction mixture was stirred for 10 minutes at 0 °C. Next,<strong>[456-24-6]2-fluoro-5-nitropyridine</strong> (450 mg, 3.17 mmol) dissolved in 1 mL of DMF was added to the reaction mixture which was allowed to stir for 15 minutes at room temperature. The mixture was then quenched with saturated ammonium chloride and extracted with EtOAc (lx). The organic layer was then washed with 10percent aq. LiC1 (3x), brine (lx), dried withsodium sulfate, filtered and concentrated to yield Intermediate I-55A, (530 mg, 2.88 mmol, 91 percent yield), as a clear oil which was was brought forward without further purification. LC-MS: Method H, MS (ESI) m/z: 185.1 (M+H)t ?H NMR (400MHz, CHLOROFORM-d) oe 9.09 (d, J2.9 Hz, 1H), 8.41 (dd, J9.0, 2.9 Hz, 1H), 6.92 (dd, J9.2, 0.4 Hz, 1H), 4.65-4.54 (m, 2H), 4.09-3.96 (m, 2H), 2.32 (t, J=5.9 Hz, 1H).
91% Ethylene glycol (0.883 mL, 15.84 mmol) was dissolved in DMF (10 mL) at 0 °C.Sodium hydride (253 mg, 6.33 mmol, 60percent in mineral oil) was added to the reaction mixture portion wise and the reaction mixture was stirred for 10 minutes at 0 °C. <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> (450 mg, 3.17 mmol) dissolved in 1 mL of DMF was then added to the reaction mixture which was allowed to stir for 15 minutes at room temperature.The mixture was then quenched with saturated ammonium chloride and extracted with EtOAc (lx). The organic layer was then washed with 10percent aqueous LiC1 (3x), brine (lx), dried with sodium sulfate, filtered and concentrated to yield Intermediate I-93A, (530 mg, 2.88 mmol, 91 percent yield), as a clear oil which was brought forward without further purification. LC-MS: Method H, MS (ESI) m/z: 185.1 (M+H)t ?H NMR(400MHz, CDC13) oe 9.09 (d, J=2.9 Hz, 1H), 8.41 (dd, J9.0, 2.9 Hz, 1H), 6.92 (dd, J=9.2,0.4 Hz, 1H), 4.65-4.54 (m, 2H), 4.09-3.96 (m, 2H), 2.32 (t, J=5.9 Hz, 1H).
  • 71
  • [ 10320-42-0 ]
  • [ 107-21-1 ]
  • 2-((5-nitropyrimidin-2-yl)oxy)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; at 80℃; for 0.333333h; <strong>[10320-42-0]2-chloro-5-nitropyrimidine</strong> (1 g, 6.27 mmol) was mixed with ethylene glycol (8ml, 143 mmol) and DIEA (3.28 ml, 18.81 mmol) was added. The mixture was stirred at80 °C for 20 minutes and was then poured into 30 mL of ice water. 40 mL of EtOAc was added to the mixture followed by 20 mL of iN aq. HC1. EtOAc (30 mL x 3) was used to extracted aq. Layer. The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated to give Intermediate I-57A in quantitative yieldas a yellow oil. The product was brought forward without further purification. ?H NMR(400MHz, CHLOROFORM-d) oe 9.33 (s, 2H), 4.73-4.51 (m, 2H), 4.08-3.96 (m, 2H), 2.41 (br. s., 1H).
100% With N-ethyl-N,N-diisopropylamine; at 80℃; for 0.333333h; <strong>[10320-42-0]2-chloro-5-nitropyrimidine</strong> (1 g, 6.27 mmol) was mixed with ethylene glycol (8 ml, 143 mmol) and DIEA (3.28 ml, 18.81 mmol) was added. The mixture was stirred at 80 °C for 20 minutes and was then poured into 30 mL of ice water. 40 mL of EtOAc was added to the mixture followed by 20 mL of IN aq. HC1. EtOAc (30 mL x 3) was used to extract the aq. layer. The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated to give I-30A in quantitative yield as a yellow oil. The product was brought forward without further purification. NMR (400MHz, CDC13) delta 9,33 (s, 2H), 4,73 - 4.51 (m, 2H), 4.08 - 3.96 (m, 2H), 2.41 (br. s, 1H).
  • 72
  • [ 118289-17-1 ]
  • [ 107-21-1 ]
  • 2-Bromo-4-[1,3]dioxolan-2-yl-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; Exemplified dye D-2-9a was synthesized in the same manner as exemplified dye D-1-1a, except that compound d-1-8 for exemplified dye D-1-1a was changed to compound d-39-1.
  • 73
  • [ 5029-67-4 ]
  • [ 301673-16-5 ]
  • [ 107-21-1 ]
  • [ 56446-64-1 ]
  • tert-butyl 3-(hydroxymethyl)-4-(pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; copper(l) iodide; In isopropyl alcohol; at 90℃; To a pressure tube; <strong>[301673-16-5]tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate</strong> (681 mg, 3.15 mmol), 2-iodopyridine (615 mg, 3 mmol), ethylene glycol (372 mg, 6 mmol) and potassium phosphate (1.28 g, 6 mmol) in isopropanol (6 ml) purged with nitrogen 5 mins were added then CuI (60 mg, 0.3 mmol) was added. The reaction was stirred and heated to 90° C. overnight. After cooling to ambient temperature MBTE (4 ml) and water (2 ml) were then added to the reaction mixture. The organic layer was extracted with MBTE (2×4 ml). The combined organic phases were washed with brine and dried over Na2SO4. The solvent was concentrated in vacuo giving 918 mg of a green oil. Purified by flash column chromatography on silica gel using gradient 0percent to 100percent MBTE in DCM. The product containing fractions were combined and reduced in vacuo to yield the title compound as a colorless gum (143 mg, 9percent). (0477) Found by 1H NMR to be a 3:5 mixture of the title product and 2-(pyridine-2-yloxy)ethan-1-ol. Used the crude product for the next stage. 1H NMR (500 MHz, Chloroform-d) delta 8.20-8.10 (m, 1.6H), 7.68-7.58 (m, 1H), 7.57-7.47 (m, 0.6H), 6.97-6.89 (m, 1H), 6.87-6.80 (m, 1H), 6.72-6.61 (m, 1.2H), 4.72-4.35 (m, 2.6H), 4.32-3.62 (m, 7H), 3.24 (d, J=7.7 Hz, 2H), 1.51 (s, 5.4H). LCMS Method 2?Tr=0.98 min, (ES+) (M+H+) 294.
  • 74
  • [ 3382-63-6 ]
  • [ 107-21-1 ]
  • C15H14FNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.7 g With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; The formula EZ-1 is a structural formula of 4-[[(4-fluorophenyl)imino]methyl]-phenol.4-[[(4-fluorophenyl)imino]methyl]-phenol (21.5 g, 0.1 mol)Soluble in 20ml DMF,Potassium carbonate (27.6 g, 0.2 mol) was added in sequenceAnd ethylene glycol (12.6g, 0.1mol),After the addition, the mixture was stirred at room temperature for 2 h.TLC judged the end of the reaction, poured the reaction solution into ice water, and filtered by suction.The filter cake was vacuum dried to give a white solid 24.7 g
23.5 g With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; <strong>[3382-63-6]4-[[(4-fluorophenyl)imino]methyl]phenol</strong> (21.5 g, 0.1 mol) was dissolved in 20 ml of DMF, followed by potassium carbonate (27.6 g, 0.2 mol) and ethylene glycol (62 g, 1 mol). After the addition was completed, the mixture was stirred at room temperature for 2 h, and the reaction was judged by TLC. The reaction mixture was poured into ice water, suction filtered, the filter cake was dried in vacuo to give a white solid 23.5g.
  • 75
  • [ 913196-43-7 ]
  • [ 4347-31-3 ]
  • [ 107-21-1 ]
  • C27H25BNO2PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform; at 50℃; for 0.5h;Inert atmosphere; General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 muL, 0.02 mmol), pinacol (0.10 M, 200 muL,0.02mmol) and 5c (0.25M, 80 muL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 muL) was added undera positive pressure of argon. The reaction was stirred at 50°C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 muL, 5.0 mumol)was added under a positive pressure of argon and thereaction stirred at 23°C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 muL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 muL, 0.20 mmol), diethyl malonate (30 muL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 mumol)were added sequentially. The reaction was stirred at 23°Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 muL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0percent isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min.
  • 76
  • [ 960128-64-7 ]
  • [ 4347-31-3 ]
  • [ 107-21-1 ]
  • C29H27BNO2PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform; at 50℃; for 0.5h;Inert atmosphere; General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 muL, 0.02 mmol), pinacol (0.10 M, 200 muL,0.02mmol) and 5c (0.25M, 80 muL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 muL) was added undera positive pressure of argon. The reaction was stirred at 50°C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 muL, 5.0 mumol)was added under a positive pressure of argon and thereaction stirred at 23°C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 muL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 muL, 0.20 mmol), diethyl malonate (30 muL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 mumol)were added sequentially. The reaction was stirred at 23°Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 muL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0percent isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min.
  • 77
  • [ 4347-31-3 ]
  • [ 107-21-1 ]
  • [ 286454-86-2 ]
  • C25H29BNO2PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform; at 50℃; for 0.5h;Inert atmosphere; General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 muL, 0.02 mmol), pinacol (0.10 M, 200 muL,0.02mmol) and 5c (0.25M, 80 muL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 muL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 muL, 5.0 mumol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 muL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 muL, 0.20 mmol), diethyl malonate (30 muL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 mumol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 muL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min.
  • 78
  • [ 131747-63-2 ]
  • [ 107-21-1 ]
  • 4-bromo-2-(1,3-dioxolan-2-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.5 g With toluene-4-sulfonic acid; In toluene; for 24h;Reflux; [0505] Step 2: Synthesis of 4-bromo-2-(1,3-dioxolan-2-yl)pyridine. To a stirred solution of 4- bromopicolinaldehyde in toluene was added ethylene glycol 4- bromo-2-(1,3-dioxolan-2-yl)pyridine 1H-NMR (400 MHz, CDCh: delta (ppm): 8.43 (d, J=5.2 Hz, 1H), 7.72 (d, J=2 Hz, 1H), 7.47-7.45 (dd, J=2 Hz, lH), 5.83 (s, lH), 4.18-4.06 (m, 4H).
  • 79
  • [ 78775-11-8 ]
  • [ 107-21-1 ]
  • 2-(4-bromo-3-methylphenyl)-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.2% With toluene-4-sulfonic acid; In toluene; at 130℃; for 12h; To a solution of <strong>[78775-11-8]4-bromo-3-methyl-benzaldehyde</strong> (2.00 g, 10.1 mmol, 1.00 equiv) in toluene (100 mL) was added TsOH-H20 (191 mg, 1.00 mmol, 0.10 equiv) and ethylene glycol (1.25 g, 20.1 mmol, 1.12 mL, 2.00 equiv). The mixture was stirred at 130 C for 12 h prior to cooling to room temperature. The pH was adjusted to 9 with DMAP and then concentrated in vacuo. The residue was purified by column chromatography (neutral Al203, petroleum ether/ethyl acetate = 1/0 to 100/1) to afford 2-(4-bromo-3 -methyl-phenyl)- 1, 3-dioxolane (2.30 g, 9.46 mmol, 94.2% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) d =7.54 (d, =8.4 Hz, 1H), 7.36 (d, J=L6 Hz, 1H), 7.17 (dd, =2.4, 8.0 Hz, 1H), 5.76 (s, 1H), 4.15 - 4.08 (m, 2H), 4.08 - 4.00 (m, 2H), 2.42 (s, 3H).
  • 80
  • [ 886364-94-9 ]
  • [ 107-21-1 ]
  • 5-bromo-2-(1,3-dioxolan-2-yl)-4-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.6% With toluene-4-sulfonic acid; In toluene; at 110℃; for 12h; To a solution of ethylene glycol (310 mg, 5.00 mmol, 280 pL, 2.00 equiv), 5-bromo-4- methyl-pyridine-2-carbaldehyde (500 mg, 2.50 mmol, 1.00 equiv) in toluene (20.0 mL) was added / oluenesul fonic acid (47.6 mg, 250 pmol, 0.10 equiv). The mixture was stirred at 110 C for 12 h and was subsequently concentrated in vacuo to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 5: 1) to afford 5-bromo- 2-(l, 3-dioxolan-2-yl)-4-methylpyridine (320 mg, 1.24 mmol, 49.6% yield) as a colorless oil. 1H NMR (400MHz, CDCI3) d = 8.64 (s, 1H), 7.42 (s, 1H), 5.80 (s, 1H), 4.19 - 4.14 (m, 2H), 4.10 - 4.05 (m, 2H), 2.42 (s, 3H).
Same Skeleton Products
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[ 107-21-1 ]

Chemical Structure| 104700-12-1

A1267930[ 104700-12-1 ]

1,2-Ethylene Glycol-13C2

Reason: Stable Isotope