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[ CAS No. 19434-34-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 19434-34-5
Chemical Structure| 19434-34-5
Chemical Structure| 19434-34-5
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Product Details of [ 19434-34-5 ]

CAS No. :19434-34-5 MDL No. :MFCD00800666
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IMPIIVKYTNMBCD-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :88060
Synonyms :

Calculated chemistry of [ 19434-34-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.35
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 3.29
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 2.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0586 mg/ml ; 0.000296 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0617 mg/ml ; 0.000311 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00489 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 19434-34-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19434-34-5 ]

* 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 [ 19434-34-5 ]

[ 19434-34-5 ] Synthesis Path-Downstream   1~94

  • 1
  • [ 75-52-5 ]
  • [ 19434-34-5 ]
  • [ 107558-81-6 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium acetate In acetic acid at 120℃; for 2h;
  • 2
  • [ 141-82-2 ]
  • [ 19434-34-5 ]
  • [ 95433-16-2 ]
YieldReaction ConditionsOperation in experiment
92% With piperidine; pyridine at 120℃; for 3h; (ii) Preparation of ortho-, meta- and para-PhO-CA General procedure: To themixture of the corresponding aldehyde (2.52 g, 12.7 mmol) andmalonic acid (1.99 g, 19.1 mmol), dry pyridine (6.5 ml) and piperidine(0.2 ml) were successively added. The mixture was stirred at120 °C for 3 h, cooled to 10 °C and acidified with HCl (~14 ml) at 1:1ratio with cooling and stirring. After 30 min, the precipitate wasfiltered, washed 3 times with H2O (20 ml) and air dried. The yieldsof o-, m- and p-PhO-CA were 92, 91 and 96%, respectively. (E)-3-(2-Phenoxyphenyl)acrylic acid (ortho-PhO-CA): 1H NMR(400 MHz, DMSO) δ 12.44 (s, 1H), 7.89 (dd, J =7.8, 1.2 Hz, 1H), 7.79(d, J =16.2 Hz, 1H), 7.46-7.35 (m, 3H), 7.21 (t, J =7.5 Hz, 1H), 7.15 (t,J= 7.4 Hz, 1H), 6.98 (d, J =7.8 Hz, 2H), 6.92 (d, J =8.1 Hz, 1H), 6.60(d, J =16.1 Hz, 1H). 13C NMR (101 MHz, DMSO) δ 167.48, 156.73,154.72, 137.50, 131.86, 130.16, 128.57, 125.62, 124.26, 123.54, 120.61, 119.41, 118.06. ESI-HRMS (m/z): Calcd for C15H12O3 [M+H]+241.0859, found 241.0861; calcd [M +NH4]+ 258.1125, found258.1128; calculated [M+Na]+ 263.0679, found 263.0683; calcd[6 M+ K]2+ 740.2212, found 740.2166; calcd [6 M+ K]+1479.4350, found 1479.4278.
With piperidine; pyridine
  • 3
  • [ 6476-32-0 ]
  • [ 19434-34-5 ]
  • 4
  • [ 13807-84-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
80% With L-alanin; silica gel; chlorochromic acid In dichloromethane at 20℃; for 15h;
78% With pyridine; chromium(VI) oxide In dichloromethane for 2h; Ambient temperature;
64% With cerium(III) chloride heptahydrate; sodium hydrogencarbonate In acetonitrile at 50℃; for 35h; Irradiation; Sealed tube; General procedure (GP1) General procedure: A 10 mL glass vial equipped with a teflon-coated stirring bar was charged with benzylic alcohol 1 (0.2 mmol), CeCl3·7H2O (10 mol %), and NaHCO3 (10 mol%). The glass vial was sealed with a PTFE septum. Then, solvent (2 mL) was added and the reaction was opened to air via a needle. The reaction was placed in a pre-programed temperature (50 °C) controlled blue LED reactor (as shown in Figure S1) and the reaction mixture was irradiated with a 455 nm blue LED. After 35-48 hours, the reaction mixture was concentrated under reduced pressure. Product 2 was purified by flash chromatography on silica using hexane and AcOEt.
With pyridinium chlorochromate In dichloromethane for 1.5h; Yield given;

  • 5
  • [ 19434-34-5 ]
  • [ 13807-84-6 ]
YieldReaction ConditionsOperation in experiment
87% With sodium tetrahydroborate In methanol at 0℃; for 0.5h; 2-Phenoxybenzylalcohol (3d) General procedure: NaBH4 (50 mg, 1.3 mmol) was added to a solution of commercial 2-phenoxybenzaldehyde (260 mg, 1.31 mmol) in MeOH (5 mL) at 0 °C. After stirring for 30 min at 0 °C, the reaction mixture was diluted with water, extracted with EtOAc, dried over MgSO4 and evaporated. The resulting residue was purified by column chromatography on silica gel (n-hexane/EtOAc = 5/1) to provide the title compound (228 mg, 1.14 mmol) in 87% yield as a colorless solid.
75.25% With methanol; sodium tetrahydroborate at 20℃; for 2.5h;
With sodium tetrahydroborate In ethanol for 16h; Ambient temperature;
With sodium tetrahydroborate In methanol at 0 - 20℃;

  • 7
  • [ 446-52-6 ]
  • [ 108-95-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 4h;
95% With potassium carbonate In N,N-dimethyl-formamide
90% With potassium carbonate In N,N-dimethyl acetamide for 2h; Reflux;
90% With potassium carbonate In 2,4-dichlorophenoxyacetic acid dimethylamine for 2h; Reflux;
87% With potassium carbonate In N,N-dimethyl acetamide for 2h; Heating;
85% With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 6h; Inert atmosphere;
85% With potassium carbonate In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;
83% With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 3h; Inert atmosphere;
82% With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 1h; Experimental procedure for the synthesis of 2-aryloxybenzaldehydes A mixture of 2-fluorobenzaldehyde (1.24 g, 10 mmol), phenol (1.12 g, 11.9 mmol), K2CO3 (3.45 g, 25 mmol) in DMF (20 mL) was placed in a pre-heated oil bath at 150 °C. The reaction mixturewas stirred at 150 °C until the reaction was complete by TLC analysis (ca. 1 h). The reaction mixture was then cooled to room temperature, diluted with water (150 mL) and extracted withethyl acetate (3 x 60 mL). Combined ethyl acetate layer was back washed with water (2 x 50 mL), brine (1 x 50 mL), dried over Na2SO4 and evaporated. The crude reaction mixture waspurified by short silica gel column chromatography using 5 % ethyl acetate in hexane as eluent to obtain 2-phenoxy benzaldehyde 1a (1.62 g, 82 % yield) as a clear oil.
79% With potassium carbonate In N,N-dimethyl-formamide at 20 - 170℃; for 2h; Inert atmosphere; Schlenk technique;
79% With potassium carbonate In N,N-dimethyl-formamide at 170℃; for 2h; Schlenk technique; Inert atmosphere; 1.a a) Preparation of 2-(4-(dimethylamino)phenoxy)benzaldehyde, 2-phenoxy- benzaldehyde and 2-(4-chlorophenoxy)benzaldehyde The benzaldehyde intermediates are synthesized following literature procedures with modifications. Into a dry Schlenk flask under argon atmosphere the corresponding phenol (17.7 mmol), 2-fluorobenzaldehyde (2.0 g, 16.1 mmol), potas- sium carbonate (5.6 g, 40.3 mmol) and anhydrous DMF (40 ml_) are added at room temperature. The mixture is warmed in a sealed flask to 170°C and stirred at this temperature for 2 h (for preparing 2-phenoxy-benzaldehyde and 2-(4- chlorophenoxy)benzaldehyde) or at 150°C for 1 .5 h (for preparing 2-(4- (dimethylamino)phenoxy)benzaldehyde). Then the mixture is allowed to cool to room temperature and is treated with water (200 ml_) and the product is extracted with diethyl ether (3^50 ml_). The combined organic layers are washed with NaOH (1 M, 50 ml_), brine (150 ml_), dried over anhydrous MgSO4 and evaporated in vacuum. The residue is purified by column chromatography (cyclohex- ane/ethyl acetate 10:1 , v/v (for preparing 2-phenoxy-benzaldehyde and 2-(4- chlorophenoxy)benzaldehyde) or used in next reaction without purification (in case of 2-(4-(dimethylamino)phenoxy)-benzaldehyde).
78.2% With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 12h;
78% With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h;
77% With potassium carbonate In N,N-dimethyl-formamide at 120℃; 2-Phenoxybenzaldehyde (7d) A solution of 2-fluorobenzaldehyde (179 μL, 1.70 mmol), phenol (152 mg, 1.62 mmol) and K2CO3 (440 mg, 3.18 mmol) in DMF (30 mL) was stirred at 120 °C overnight. After cooling to room temperature, the reaction mixture was diluted with water, extracted with EtOAc, dried over MgSO4 and evaporated. Purification of the residue by column chromatography on silica gel (n-hexane/EtOAc = 5/1) provided the title compound (260 mg, 1.31 mmol) in 77% yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 10.53 (s, 1H), 7.94 (dd, J = 8.0 Hz, 1.6 Hz, 1H), 7.51 (ddd, J = 8.4 Hz, 7.2 Hz, 2.0 Hz, 1H), 7.42-7.37 (m, 2H), 7.21-7.17 (m, 2H), 7.07 (dd, J = 8.8 Hz, 1.2 Hz, 2H), 6.90 (dd, J = 8.4 Hz, 0.8 Hz, 1H).
75% With potassium carbonate In ISOPROPYLAMIDE for 16h; Heating / reflux; 95.i EXAMPLE 95: N-(3T3-DIMETHYLBUTVL)-N-[(2-PHENOXYPHENSL) METHYLLPIPERIDIN-4-AMINE FUMARATE; (i) To a 250 ml round bottomed flask was added 2-fluorobenzaldehyde (12.4 g, 100 mmole, 1.0 eq. ), phenol (11.3 g, 120 mmole, 1.2 eq. ), potassium carbonate (16.6 g, 120 mmole, 1.2 eq. ) and DIMETHYLACETAMIDE (100 ml). The reaction mixture was heated at reflux for 16 hours. The mixture was then diluted with water and extracted with diethyl ether. The combined organic extracts were washed with water (3x) and brine. The washed extracts were dried (NA2SO4) and concentrated IN VACUO to give a yellow oil (15.7 g). This was purified by automated flash chromatography using an ISCO Combiflash system (SI02 (120 g x 2); 0-10% ethyl acetate in cyclohexane gradient elution over 40 minutes) to give 2-PHENOXYBENZALDEHYDE as a colourless oil (14.8 g, 75%). SN (300 MHz, CDC13) 10.52 (1H, s, CHO), 7.94 (1H, dd, ArH), 7.54-7. 45 (1H, m, ArH), 7.42-7. 36 (2H, m, ArH), 7.21-7. 15 (2H, m, ArH), 7.09-7. 04 (2H, m, ArH), 6.90 (1H, d, ArH); LCMS 6 min, Rt == 4.0 min, (M++1) = 199.
75% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18h; 1.1 Step 1: Synthesis of 2-phenoxybenzaldehyde O-fluorobenzaldehyde (2.48g, 20.00mmol), phenol (1.88g, 20.00mmol),Potassium carbonate (11.00g, 80.00mmol) and N, N-dimethylformamide (30mL) were added to a 250mL single-necked flask, and the reaction was stirred in an oil bath at 60 ° C for 18h.Add ice water (200 mL) to the reaction solution and stir for 10 min.Wash the filter cake with water (50mLx3),The title compound (yellow solid, 2.97 g,Yield: 75%).
72% With potassium carbonate In N,N-dimethyl-formamide for 13h; Reflux;
67% With potassium carbonate In ISOPROPYLAMIDE at 120℃; for 6h; 1.1 Phenol (50 g; 0.531 mol), potassium carbonate (80.7 g; 0.584 mol) and then dimethylacetamide (300 mL) are introduced into a 100 ml three-necked flask under argon. 2-Fluorobenzaldehyde (55.9 mL; 0.531 mol) is then added. The reaction medium is heterogeneous and slightly yellow. This mixture is heated at 120° C. for 6 hours. After cooling to room temperature, the medium is diluted with water and extracted twice with dichloromethane. The organic phase is washed with 5% sodium hydrogen carbonate solution and then with water and finally with saturated sodium chloride solution. It is then dried over sodium sulfate and then filtered and concentrated to the maximum. The brown-yellow oil obtained is distilled under vacuum with heating. 70 g of a slightly yellow oil are obtained (yield: 67%).
67% With potassium carbonate In ISOPROPYLAMIDE at 120℃; for 6h; 1.1 Phenol (50 g; 0.531 mol), potassium carbonate (80.7 g; 0.584 mol) and then dimethylacetamide (300 mL) are introduced into a 100 mL three-necked flask under argon. 2-Fluorobenzaldehyde (55.9 mL; 0.531 mol) is then added. The reaction medium is heterogeneous and slightly yellow. This mixture is heated at 120° C. for 6 hours. After cooling to room temperature, the medium is diluted with water and extracted twice with dichloromethane. The organic phase is washed with 5% sodium hydrogen carbonate solution and then with water and finally with saturated sodium chloride solution. It is then dried over sodium sulfate and then filtered and concentrated to the maximum. The brown-yellow oil obtained is distilled under vacuum with heating. 70 g of a slightly yellow oil are obtained (yield: 67%).
57% With potassium carbonate In N,N-dimethyl-formamide (Additional Experimental Method) 2-Phenoxybenzaldehyde As in Reaction Scheme 4, commercially available2-fluorobenzaldehyde (200 mg, 1.61 mmol) was used as a starting material. Phenol (152 mg, 1.61 mmol) was nucleophilically added using potassium carbonate (245 mg, 1.77 mmol) base in the presence of DMF (3 ml) solvent, thereby synthesizing 2-phenoxy benzaldehyde (183 mg, 0.92 mmol). (Yield: 57%)
50% Stage #1: phenol With potassium carbonate In tetrahydrofuran for 1h; Reflux; Stage #2: 2-Fluorobenzaldehyde In tetrahydrofuran for 24h; Reflux; 10 2-Phenoxybenzaldehyde (26a) Example 10 Synthesis of Compound 26 2-Phenoxybenzaldehyde (26a) K2CO3 (22 g, 159 mmol) was added to a stirred solution of phenol (7.60 g, 81 mmol) in THF (100 mL) at reflux. After 1 h 2-fluorobenzaldehyde (8.49 mL, 101 mmol) was added and the reaction mixture was refluxed for an additional 24 h. Upon completion the mixture was cooled down to rt, concentrated in vacuo, saturated NaHCO3 (100 mL) was added and product was extracted using EtOAc (3 x 80 mL). The combined organic layers were washed with brine, dried, concentrated in vacuo and purified by flash chromatography to yield 2-phenoxybenzaldehyde (8.05 g, 40,6 mmol, 50%). 1H NMR (CDCl3, 400 MHz): δ 10.52 (s, 1 H), 7.94 (dd, J = 7.8, 1.8 Hz, 1 H), 7.54 - 7.48 (m, 1 H), 7.43 - 7.36 (m, 2H), 7.22 - 7.15 (m, 2H), 7.10 - 7.04 (m, 2H), 6.90 (d, J = 8.4, 1 H). Spectroscopic data are in agreement with those reported in literature6.
With potassium carbonate In N,N-dimethyl acetamide at 155℃;
With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 2h;
With potassium carbonate In hexane; N,N-dimethyl acetamide; water; ethyl acetate 19.A 8-(2-phenoxy-benzyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one HCl Salt (Compound # 57) Step A: (Yaeger, et al. Synthesis, 1995, pp28) To a solution of phenol (1.8888 g, 0.0201 mol) and 2-fluorobenzaldehyde (2.14 mL, 0.0203 mol) in N,N-dimethylacetamide (20 mL) was added anhydrous K2CO3 (3.0798 g, 0.0223 mol). The resulting heterogenous mixture was refluxed for 3 h. The resulting green mixture was then treated with H2O (100 mL) and extracted with EtOAc (2*100 mL). The combined organic extracts were washed with H2O (4*100 mL), dried over Na2SO4, filtered and concentrated. The resulting dark residue was purified by flash chromatography on silica gel (10% EtOAc in hexane) to yield 2-phenoxybenzaldehyde as a light yellow oil. 1H NMR (300 MHz, DMSO d6) δ 6.91 (m, 1H), 7.15 (m, 2H), 7.19-7.25 (m, 2H), 7.45-7.55 (m, 2H), 7.65-7.70 (m, 1H), 7.85-7.90 (m, 1H).
With potassium carbonate In N,N-dimethyl-formamide at 100℃;
With potassium carbonate In N,N-dimethyl-formamide at 100℃; 54.1 1) Production of 2-phenoxybenzaldehyde To a solution of 2-fluorobenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 676 mg of phenol and 993 mg of potassium carbonate were added, and the reaction solution was stirred overnight at 100°C. The reaction solution was cooled, then 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a pale yellow oil.
Inert atmosphere;
With potassium carbonate In dimethyl amine for 2.5h; Reflux;
With potassium carbonate In N,N-dimethyl acetamide at 170℃;
With potassium carbonate In N,N-dimethyl acetamide for 3h; Reflux; 19.A Step A Example 19 (Reference) 8-(2-phenoxy-benzyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one HCl Salt (Compound 57) Step A: (Yaeger, et al. Synthesis, 1995, pp28) To a solution of phenol (1.8888 g, 0.0201 mol) and 2-fluorobenzaldehyde (2.14 mL, 0.0203 mol) in N,N-dimethylacetamide (20 mL) was added anhydrous K2CO3 (3.0798 g, 0.0223 mol). The resulting heterogenous mixture was refluxed for 3h. The resulting green mixture was then treated with H2O (100 mL) and extracted with EtOAc (2x100 mL). The combined organic extracts were washed with H2O (4x 100 mL), dried over Na2SO4, filtered and concentrated. The resulting dark residue was purified by flash chromatography on silica gel (10% EtOAc in hexane) to yield 2-phenoxybenzaldehyde as a light yellow oil. 1H NMR (300 MHz, DMSO d6) δ 6.91 (m, 1 H), 7.15 (m, 2H), 7.19- 7.25 (m, 2H), 7.45-7.55 (m, 2H), 7.65-7.70 (m, 1 H), 7.85-7.90 (m, 1 H).
With caesium carbonate In N,N-dimethyl acetamide at 150℃; for 2h;

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  • 8
  • [ 19434-34-5 ]
  • 2-phenoxybenzaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With pyridine; hydroxylamine hydrochloride In ethanol for 1h; Heating;
86% With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 0.166667h;
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; Aldoximes; General Procedure General procedure: To a solution of the aldehyde in CH2Cl2 (0.2 M) was added hydroxylamine hydrochloride (2.0 equiv) and Et3N (4.2 equiv) and the mixture was stirred at r.t. for 16 h. The reaction was quenched with sat. aq NaHCO3 and extracted with CH2Cl2. The combined organic layers were washed with aq 1 M HCl, dried (MgSO4), and concentrated to give the crude aldoxime, which was purified by flash chromatography. The known aldoximes 1,18 4a,5i 4b,19 4c,20 4d,18 4e,21 4f,22 4g,18 4h,23 4i,244j,20 7,25 10a,25 10b,26 10c,18 10d,27 10e,27 10f,28 10j,5i and 1929 were synthesized following the general procedure described above.
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water Synthesis of Aldoximes General procedure: To a mixture of hydroxylamine hydrochloride (15.88 mmol, 1.2 equiv)in EtOH (4 mL) and water (20 mL) was added sodium carbonate(15.88 mmol, 1.2 equiv) and the mixture was stirred for 5 min to obtaina clear solution. To this, the appropriate aldehyde (13.23 mmol,1.0 equiv) was added and the solution was stirred at r.t. for 0.5-1 h;the progress of the reaction was monitored by TLC. After addition ofwater (30 mL), the resulting solids were filtered and dried to obtainthe corresponding aldoximes. When the solid did not precipitate outof the reaction, the reaction mixture was extracted with EtOAc(2 × 50 mL). The combined organic layers were dried over anhydroussodium sulfate, filtered and evaporated under reduced pressure to obtainthe corresponding aldoximes, which were used without furtherpurification.

  • 9
  • [ 209412-67-9 ]
  • [ 6476-32-0 ]
  • [ 19434-34-5 ]
  • 2-phenoxybenzaldehyde O-(tert-butyl)oxime [ No CAS ]
  • 2-phenoxybenzaldehyde O-(tert-butoxymethyl)oxime [ No CAS ]
  • 10
  • [ 364354-24-5 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
61% With potassium carbonate In various solvent(s) at 130℃; for 16h;
  • 11
  • [ 89-98-5 ]
  • [ 108-95-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; tert-butyl XPhos In toluene at 110℃; for 22h;
62% With potassium phosphate; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole; palladium diacetate In toluene at 100℃; for 10h; Inert atmosphere;
61% With potassium carbonate In dimethyl sulfoxide at 20℃;
60% With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;
52% With tetrabutylammomium bromide; caesium carbonate In N,N-dimethyl-formamide at 145℃; for 24h; Inert atmosphere; 2.3 General procedure for CuO-Fe3O4-catalyzed O-arylation of phenols with aryl halides General procedure: To a stirred solution of phenol (2.2mmol) in DMF (15.0mL) under an argon atmosphere were added CuO-Fe3O4 (0.2mmol), TBAB (0.2mmol), Cs2CO3 (326mg, 1.0mmol) and aryl halide (2.0mmol). The reaction mixture was stirred at the required temperature (145°C) for 24 h. At the end of reaction, the catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The residue was purified by column chromatography on silica gel to afford the desired product.
50% With copper(I) oxide; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; Green chemistry; General procedure for the synthesis of diarylethers by using Cu2O/Cu-CNTsas a catalyst General procedure: In an oven-dried 50 mL round-bottomed flask with a condenser, phenol (1.0 mmol),bromobenzene (1.2 mmol), Cs2CO3 (1.0 mmol) and Cu2O/Cu-CNTs catalyst (0.06 g) were addedunder nitrogen atmosphere, followed by addition of DMSO (10 mL). The reaction mixture washeated in an oil bath at 140 and stirred at this temperature for 24 h. After the completion of thereaction (monitored by TLC), the reaction mixture was filtered. The filtrate was extracted withethyl acetate (3×10 mL) by adding a small amount of saturated aqueous NaCl solution. Theorganic layer was dried with anhydrous MgSO4 and concentrated to get the crude product. Theresulting residue was purified by column chromatography on silica gel to provide the desiredproduct.
With potassium carbonate In N,N-dimethyl-formamide at 150℃; Experimental procedure for the synthesis of 2-aryloxybenzaldehyde: General procedure: A mixture of 2-chloroquinoline-3-carbaldehyde A (383 mg, 2.0 mmol), 4-isopropyl-3-methylphenol B (451 mg, 3.0 mmol), K 2 CO 3 (692 mg, 5.0 mmol) in dry DMF (4 mL) was stirred in a pre-heated oil bath at 150 oC until the reaction was complete by TLC analysis (ca. 2 h). After cooling to room temperature, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3 x 25 mL). Combined ethyl acetate layer was back washed with water (2 x 25 mL), brine (1 x 15 mL), dried over Na 2 SO 4 and evaporated. The crude product was purified by short silica gel column chromatography using 2→5% ethyl acetate in hexanes as eluent to obtain 2-(4-isopropyl-3-methylphenoxy)quinoline-3-carbaldehyde C (440 mg, 72% yield) as light brown viscous oil.

  • 12
  • [ 6630-33-7 ]
  • [ 108-95-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In water for 2h; Reflux; Green chemistry;
81% With potassium phosphate; tert-butyl XPhos In toluene at 110℃;
77% With sodium hydroxide In water at 80℃; for 3h;
76% With potassium carbonate In dimethyl sulfoxide at 20℃;
75% With C19H18ClFeNPdSe; caesium carbonate In dimethyl sulfoxide at 110℃; for 6h;
73% With C15H16BrCl2NPdSe; potassium carbonate In dimethyl sulfoxide at 110℃; General Procedure for O-Arylation of Phenol. General procedure: An oven-dried10 mL pressure tube was charged with aryl bromide (1.0 mmol),phenol (1.2 mmol), K2CO3 (2.5.0 mmol), DMSO (3.0 mL), and catalyst (5 or 6). The reaction mixture was stirred and heated at 110 °C in open air conditions for 16 h. Thereafter reaction mixture was cooled to room temperature and 25 mL of distilled water was added. The resulting mixture was extracted with ethyl acetate(2 25 mL). The organic layer was washed with water(2 x 25 mL) and dried over anhydrous Na2SO4. The solvent of theextract was removed with rotary evaporator and the resulting residuewas purified by column chromatography on silica 60 (1 x 12 cm) using ethyl acetate and hexane mixture as eluent. Pure products were authenticated by 1H NMR and their data are presented in the supporting information.
68% With potassium phosphate; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole; palladium diacetate In toluene at 100℃; for 10h; Inert atmosphere;
61% With pyridine; quinoline; potassium carbonate; copper(II) oxide at 170℃;
60% With copper(II) oxide; potassium hydroxide In N,N-dimethyl acetamide at 27℃; for 24h; Inert atmosphere; Sealed tube; Procedure for C-O/C-S cross coupling General procedure: A magnetic stirring bar, nanocrystalline CuO (10 mg, 3 mol %), KOH (112 mg, 2 mmol) and phenol/substituted phenol/ thiophenol (1.2 mmol) were added into an oven-dried flask (25 mL). The flask was sealed with a septum, followed by three cycles of evacuation and filling with dry nitrogen. Then aryl halide (1 mmol) and N,N-dimethyl acetamide (DMAc) (4 mL) were injected through a syringe. The flask was sealed and stirred under nitrogen until the completion of the reaction (as monitored by TLC or GC). The catalyst was recovered from the reaction mixture and washed several times with ethyl acetate. The catalyst-free reaction mixture was quenched with brine solution and the product was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate, 80/20) to afford the product with high purity.

  • 13
  • [ 615-43-0 ]
  • [ 19434-34-5 ]
  • C19H14INO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate In toluene at 100℃;
  • 14
  • [ 19434-34-5 ]
  • [ 90-47-1 ]
YieldReaction ConditionsOperation in experiment
93% With tert.-butylhydroperoxide; rhodium(III) chloride; triphenylphosphine In chlorobenzene at 160℃; for 24h; Inert atmosphere;
89% With copper; Selectfluor In acetonitrile at 100℃; for 24h; 1 0.3 mmol of 2-phenoxybenzaldehyde (59.4 mg), 0.03 mmol of Cu powder (1.92 mg), and 0.6 mmol of Selectfluor (212.4 mg) were placed in a 15 mL thick-walled pressure-resistant reaction tube, and then 3 mL of acetonitrile was added as a solvent.Then, magnetic stirring was carried out at 100 ° C for 24 hours.After cooling to room temperature. After completion of the reaction, 10mL of water was added, extracted with dichloromethane (3 * 10mL), the organic phases were combined and dried over anhydrous Na2SO4,After the filtrate was removed by filtration, the filtrate was separated by silica gel column chromatography, eluting with a petroleum ether/ethyl acetate ratio of 20:1 as an eluent, and the eluent containing the product was collected to evaporate the solvent to obtain a xanthone.This material was a white solid with a yield of 89%.
89% With water; copper; Selectfluor In acetonitrile at 100℃; for 24h; 4.3. Typical experimental procedure for the synthesis of xanthones 2 from 1 General procedure: 1 (0.3 mmol), Cu(0) powder (1.92 mg, 10 mol %), Selectfluor (212.6 mg, 0.6 mmol, 2 equiv), and MeCN (water content: 0.05 w/w %, 3 mL) were added to a 25-mL flask. Then the reaction mixture was stirred at 100 °C for 24 h. Upon completion, the resulting mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (20/1, V/V) as eluent to give pure 2. 4.3.1. 9H-xanthen-9-one (2a)[13] Purification by column chromatography (petroleum ether/ EtOAc, 20/1) as a white solid (52.4 mg, 89%); m.p. 180-182 °C (lit. [13]mp179-180 °C); IR (neat): ν = 1654 (C=O) cm-1; 1H NMR (CDCl3, 500 MHz): δ 8.37 (dd, J1 = 8.0 Hz, J2 = 1.5 Hz, 1H), 7.77-7.74 (m, 1H), 7.52 (d, J = 8.0 Hz, 1H), 7.41 (t, J = 7.5 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δ 177.3, 156.3, 134.8, 126.8, 123.9, 121.9, 118.0.
86% Stage #1: 2-(phenoxy)benzaldehyde With titanium tetrachloride In dichloromethane at 20℃; for 24h; Stage #2: With chromium(VI) oxide; periodic acid In acetonitrile for 1h;
65% With tert.-butylhydroperoxide; tetrabutylammomium bromide In water at 120℃; for 24h; Schlenk technique; Sealed tube;
60% With tert.-butylhydroperoxide; tetrabutylammomium bromide In water at 120℃; Schlenk technique; Sealed tube;
60% With carbon tetrabromide; oxygen In neat (no solvent) at 140℃; for 0.333333h;
55% With tert.-butylhydroperoxide; ferrocene In water; acetonitrile at 20 - 90℃; for 24h;
52% With dipotassium peroxodisulfate; tetraethylammonium bromide In 1,2-dichloro-ethane at 120℃; for 36h; Inert atmosphere;
Multi-step reaction with 3 steps 1: MgSO4 / toluene / 100 °C 2: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 24 h / 100 °C 3: aq. HCl / acetone
Multi-step reaction with 3 steps 1: concentrated aqueous KOH / 60 °C 2: thionyl chloride 3: toluene; palladium/barium sulfate / Hydrogenation
Multi-step reaction with 2 steps 1: copper diacetate / toluene / Reflux 2: copper(II) bis(trifluoromethanesulfonate) / toluene / 80 °C
Multi-step reaction with 2 steps 1.1: magnesium sulfate / dichloromethane / 10 h / 20 °C 2.1: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 26 h / 80 °C 2.2: 20 °C

  • 15
  • [ 19434-34-5 ]
  • [ 61744-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: MgSO4 / toluene / 100 °C 2: cesium pivalate / Pd(OAc)2; 1,1-bis(diphenylphosphino)methane / dimethylformamide / 24 h / 100 °C
  • 16
  • [ 374538-01-9 ]
  • [ 19434-34-5 ]
  • 17
  • [ 443776-94-1 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / N,N-dimethyl-acetamide / 16 h / 110 °C 2: 61 percent / K2CO3 / trans-di-μ-acetobis[2-(di-o-tolylphosphino)benzyl]Pd(II)2 / various solvent(s) / 16 h / 130 °C
  • 19
  • [ 19434-34-5 ]
  • (1R,2R)-2-[3-(2-Phenoxy-phenyl)-propionyl]-cyclopropanecarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaH / tetrahydrofuran / Heating 2: H2 / 5percent Pd/C / ethanol / 775.7 Torr / Ambient temperature 3: aq. NaOH / ethanol / 70 °C
  • 21
  • C22H28N3O4Pol [ No CAS ]
  • [ 19434-34-5 ]
  • C35H36N3O5Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In ethanol at 20℃; for 60h; 9; iv Example 9; Preparation of a Compound Library on Solid Support A small compound library of five compounds was used to demonstrate the use of the compounds and supported linkers of the invention. [00098] The library was prepared according to the scheme below. Conditions: i). 2 eq. of 1 (corresponding to the loadings on solid phase) in DMF, RT, 24 hrs. ii), 5 eq. N-hydroxysuccinimide (NHS) and diisopropylcarbodiimide (DIC) in DMF, RT 24 hrs, then 5 eq. piperazine RT 24 hrs. iii), 3 eq. HBTU, 3 eq. p-acetyl benzoic acid and 10 eq. N-methylmorpholine (NMM), DMF, RT 5 hrs. iv), 5 eq. aldehydes, 1 eq. sodium methoxide in EtOH, RT, 60 hrs. v), 5 eq. N-methyl isatin and (2-fluorophenyl) glycine, in dioxane/water (5/1), RT, 60 hrs. vi), 0.1M Iodine in THF /water (4/1), RT, 1 hr. [00100] Thus, after covalent attachment of the linker moiety to the activated solid support (agarose or polystyrene) to form resin 6, standard amide bond formation (ii, iii; 6 to 8) was used to functionalize the resin. The functionalized resin 8 was divided into 5 portions and reacted with 5 different aldehydes (2-fluorobenzaldehyde, 3-formylbenzofuran, 2-phenoxybenzaldehyde, 2-(4'-chlorophenyl)thiobenzaldehyde and 5-(2'-chlorophenyl)-2-furaldehyde) to form chalcones 9. The resin portions were then pooled together and reacted with N-methyl isatin and (2-fluorophenyl) glycine to give spiro compounds 10. After cleavage with iodine/water/THF, compounds 11 were released and excess iodine was reduced with sodium sulfite. Analysis of the reaction mixture by HPLC showed 5 peaks for the five compounds in the mixture. LC-MS analysis gave the correct molecular weight for each compound.
  • 22
  • [ 710974-71-3 ]
  • [ 19434-34-5 ]
  • 1,1-dimethylethyl 4-[(2-phenoxyphenylmethyl)(3-methylbutyl)amino]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane at 20℃; for 72h; 6A.ii To a solution of 1, 1-dimethylethyl 4- [ (3-METHYLBUTYL) amino] piperidine-1- carboxylate in 1,2-dichloroethane (10 ml) was added 2-PHENOXYBENZALDEHYDE. To this was added a solution of sodium triacetoxyborohydride (3.0 eq. ) in DIMETHYLFORMAMIDE (2 ml). This mixture was left to stir for 3 days under nitrogen, at room temperature. To the reaction mixture was added water (10 ml) and the mixture stirred vigorously for several minutes. The chlorinated organic layer was run through a hydrophobic frit to remove water, diluted with methanol (10 ml) and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml) then basic material eluted with 2N ammonia in methanol. The AMMONIA/METHANOL solution was concentrated in vacuo to give 1,1- DIMETHYLETHYL 4-[(2-PHENOXYPHENYLMETHYL) (3-METHYLBUTYL) amino] piperidine-1- carboxylate as a colourless oil. To a solution of this oil in dichloromethane (10 ml) was added trifluoroacetic acid (TFA) (15 EQ). The solution was stirred overnight at room temperature. Solvent and TFA were removed in vacuo. The resulting oil was taken up in methanol and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml). Basic material was then eluted using 2M ammonia in methanol (50 ml). Removal of solvent from the AMMONIA/METHANOL mixture under vacuum, gave a colourless oil. The oil was taken up in methanol. To this solution was added a solution of fumaric acid (1 eq) in methanol. The mixture was left to stir for a couple of minutes, then ethyl acetate and cyclohexane were added. The resulting precipitate was collected by filtration to give the title compound as a white solid (0.264 g, 30%). 8H (300 MHz, MEOD) 7.46 (1H, dd, ArH), 7.26-7. 16 (3H, m, ArH), 7.10-7. 04 (1H, m, ArH), 7.00-6. 95 (1H, m, ArH), 6.86-6. 79 (3H, m, ArH), 6.61 (4H, s, fumarate CH), 3.68 (2H, s, CH2AR), 3.33-3. 28 (2H, m, NCH2), 3.04-2. 96 (3H, m, NCH, NCH2), 2.56-2. 51 (2H, m, NCH2), 1.91-1. 87 (2H, m, CCH2), 1.76-1. 62 (2H, m, CCH2), 1.52-1. 41 (1H, m, CH), 1.30-1. 23 (2H, m, CH2), 0.74 (6H, d, CH3) ; LCMS 12 min, Rt = 4.2 min, (M++ 1) = 353.
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane at 20℃; for 72h; 6A.ii (ii) To a solution of 1,1-dimethylethyl 4- [ (3-methylbutyl) amino] piperidine-1- carboxylate in 1,2-dichloroethane (10 ml) was added 2-phenoxybenzaldehyde. To this was added a solution of sodium triacetoxyborohydride (3.0 eq. ) in dimethylformamide (2 ml). This mixture was left to stir for 3 days under nitrogen, at room temperature. To the reaction mixture was added water (10 ml) and the mixture stirred vigorously for several minutes. The chlorinated organic layer was run through a hydrophobic frit to remove water, diluted with methanol (10 ml) and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ML) then basic material eluted with 2N ammonia in methanol. The ammonia/methanol solution was concentrated I71 VACUO to give 1,1- dimethylethyl 4-[(2-PHENOXYPHENYLMETHYL) (3-METHYLBUTYL) AMINO] PIPERIDINE-1- carboxylate as a colourless oil. To a solution of this oil in dichloromethane (10 ml) was added trifluoroacetic acid (TFA) (15 EQ). The solution was stirred overnight at room temperature. Solvent and TFA were removed III vacuo. The resulting oil was taken up in methanol and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml). Basic material was then eluted using 2M ammonia in methanol (50 ml). Removal of solvent from the ammonia/methanol mixture under vacuum, gave a colourless oil. The oil was taken up in methanol. To this solution was added a solution of fumaric acid (1 EQ) in methanol. The mixture was left to stir for a couple of minutes, then ethyl acetate and cyclohexane were added. The resulting precipitate was collected by filtration to give the title compound as a white solid (0.264 g, 30%). 8H (300 MHz, MEOD) 7.46 (1H, dd, ArH), 7.26-7. 16 (3H, m, ArH), 7.10-7. 04 (1H, M, ArH), 7.00-6. 95 (1H, m, ArH), 6.86-6. 79 (3H, m, ArH), 6.61 (4H, s, fumarate CH), 3.68 (2H, s, CH2Ar), 3.33-3. 28 (2H, m, NCH2), 3.04-2. 96 (3H, m, NCH, NCH2), 2.56-2. 51 (2H, m, NCH2), 1.91-1. 87 (2H, m, CCH2), 1.76-1. 62 (2H, m, CCH2), 1.52-1. 41 (1H, M, CH), 1.30-1. 23 (2H, m, CH2), 0.74 (6H, d, CH3) ; LCMS 12 min, Rt = 4.2 min, (M++1) = 353.
Stage #1: 4-(3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester; 2-(phenoxy)benzaldehyde With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane at 20℃; for 72h; Stage #2: With water In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane 6A.ii To a solution of 1, 1-dimethylethyl 4- [ (3-methylbutyl) amino] piperidine-1- carboxylate in 1, 2-dichloroethane (10 ml) was added 2-phenoxybenzaldehyde. To this was added a solution of sodium triacetoxyborohydride (3.0 eq. ) in dimethylformamide (2 ml). This mixture was left to stir for 3 days under nitrogen, at room temperature. To the reaction mixture was added water (10 ml) and the mixture stirred vigorously for several minutes. The chlorinated organic layer was run through a hydrophobic frit to remove water, diluted with methanol (10 ml) and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml) then basic material eluted with 2N ammonia in methanol. The ammonia/methanol solution was concentrated in vacuo to give 1,1- dimethylethyl 4-[(2-phenoxyphenylmethyl) (3-methylbutyl) amino] piperidine-1- carboxylate as a colourless oil. To a solution of this oil in dichloromethane (10 ml) was added trifluoroacetic acid (TFA) (15 eq). The solution was stirred overnight at room temperature. Solvent and TFA were removed in vacuo. The resulting oil was taken up in methanol and loaded onto an SCX-2 (10 g) column. The column was washed with methanol (50 ml). Basic material was then eluted using 2M ammonia in methanol (50 ml). Removal of solvent from the ammonia/methanol mixture under vacuum, gave a colourless oil. The oil was taken up in methanol. To this solution was added a solution of fumaric acid (1 eq) in methanol. The mixture was left to stir for a couple of minutes, then ethyl acetate and cyclohexane were added. The resulting precipitate was collected by filtration to give the title compound as a white solid (0.264 g, 30%)-aH (300 MHz, MeOD) 7.46 (1H, dd, ArH), 7.26-7. 16 (3H, m, ArH), 7.10-7. 04 (1H, m, ArH), 7. 00-6. 95 (1H, m, ArH), 6.86-6. 79 (3H, m, ArH), 6.61 (4H, s, fumarate CH), 3.68 (2H, s, CHAR), 3.33-3. 28 (2H, m, NCH2), 3.04-2. 96 (3H, m, NCH, NCH,), 2.56-2. 51 (2H, m, NCH,), 1.91-1. 87 (2H, m, CCH,), 1.76-1. 62 (2H, m,'CCH2), 1. 52-1.41 (1H, m, CH), 1.30-1. 23 (2H, m, CH,), 0.74 (6H, d, CH3); LCMS 12 min, Rt = 4.2 min, (M++1) = 353.
  • 23
  • [ 19434-34-5 ]
  • [ 144-55-8 ]
  • [ 1021-25-6 ]
  • 8-(2-phenoxy-benzyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one HCl Salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium tris(acetoxy)borohydride In diethyl ether; chloroform; 1,2-dichloro-ethane 19.B Step B Step B To a mixture of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (291 mg, 1.26 mmol) and 2-phenoxybenzaldehyde (299 mg, 1.50 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (454 mg, 2.14 mmol). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 20 h. The reaction mixture was then quenched with 1 N aqueous NaHCO3 and extracted with CHCl3 (100 mL). The combined extracts were dried over Na2SO4, filtered and concentrated. The isolated solid was purified by flash chromatography on silica gel to yield the title compound as a free base. The free base was dissolved in CHCl3 (35 mL), and treated with 2.5 mL of 1 N HCl in Et2O. The corresponding HCl salt was precipitated by addition of Et2O, then collected by filtration and dried the vacuum oven at 50° C. for 18 h to yield the title product as an amorphous solid. MS (loop pos): MH+=414.1 (100%). 1H NMR (300 MHz, DMSO d6) δ 1.85-1.95 (m, 1H), 2.90-3.10 (m, 2H), 3.35-3.60 (m, 2H), 3.70-3.85 (m, 2H), 4.35-4.45 (m, 2H), 4.60 (s, 2H), 7.05-7.20 (m, 4H), 7.25-7.35 (m, 4H, 7.45-7.55 (m, 3H), 7.85-7.90 (m, 1H), 9.00 (s, 1H), 10.9 (s, 1H)
  • 24
  • [ 19434-34-5 ]
  • 2-phenoxybenzaldoxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride In methanol; water R.9 Production of 2-phenoxybenzaldoxime REFERENCE EXAMPLE 9 Production of 2-phenoxybenzaldoxime To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. 1 H-NMR (CDCl3) δ ppm: 6.88-7.41 (m, 8H), 7.45 (s, 1H), 7.86 (dd, 1H, J=7.9., 2.0), 8.49 (s, 1H)
With hydroxylamine hydrochloride In methanol; water R.9 Production of 2-phenoxybenzaldoxime Reference Example 9 Production of 2-phenoxybenzaldoxime To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. 1 H-NMR (CDC13) δppm: 6.88-7.41 (m, 8H), 7.45 (s, 1H), 7.86 (dd, 1H, J=7.9., 2.0), 8.49 (s, 1H)
With hydroxylamine hydrochloride In methanol; water R.9 Production of 2-phenoxybenzaldoxime Reference Example 9 Production of 2-phenoxybenzaldoxime To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. 1 H-NMR (CDCl3) δ ppm: 6.88-7.41 (M, 8H), 7.45 (s, 1H), 7.86 (dd, 1H, J=7.9., 2.0), 8.49 (s, 1H).
  • 25
  • [ 236406-47-6 ]
  • [ 19434-34-5 ]
  • [ 912464-68-7 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 24h; a) t°rMmty^-^-phenoxybenzyty-S^-diazaspirotS^undecane-theta-carboxylate tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (0.95 g, 3.26 mmol), 2-phenoxybenzaldehyde (0.70 g, 3.54 mmol) and sodium triacetoxyborohydride (0.97 g, 4.56 mmol) were stirred in a mixture Of CH2Cl2 (20 mL), DMF (LO mL) and Et3N (0.68 mL) for 24h at room temperature. Na2CO3 (aq.sat) (30 mL) was added to the reaction mixture. The product was extracted with CH2Cl2, washed with water, dried and the solvent was evaporated. Column cromatography on SiO2 with heptane/EtOAc 1:1 with 2% Et3N gave the title compound (384 mg).1H NMR (400 MHz, CDC13): delta 7.52 (m, IH), 7.29 (m, 3H), 7.14 (m,lH), 7.06 (m, IH), 6.91 (m, 3H), 3.59 (m, 2H), 3.35 (m, 4H), 1.45 (s, 9H), 1.69-1.32 (m, 4H)
  • 26
  • [ 19434-34-5 ]
  • [ 205931-74-4 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-(phenoxy)benzaldehyde In tetrahydrofuran at 20℃; for 4h; A solution of 2-phenoxybenzoic acid (660 mg, 3.08 mmoles) and N,O-dimethylhydroxylamine hydrochloride (451 mg, 4.62 mmoles) in DMF (15 ml) was treated at rt for 18 h with triethylamine (1.3 ml, 9.24 mmoles) and HBTU (1.75 g, 4.62 mmoles). The reaction mixture was partitioned between 1N NaOH and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford 1 which was not further purified (827 mg, 100%). A 1M solution of lithium aluminum hydride in THF (3.18 ml, 3.18 mmoles) was slowly added to a cold (-20° C.) solution of 1 (410 mg, 1.59 mmoles) in THF (8 ml). The solution was stirred at -20° C. for 45 min and then quenched slowly with water. The mixture was filtered through a cake of celite and the filtrate was partitioned between ethyl acetate and saturated bicarbonate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford aldehyde 2 (278 mg, 88%) which was not further purified. A solution of triethylphosphonoacetate (0.334 ml, 1.68 mmoles) in THF (2 ml) was treated with 60% sodium hydride (132 mg, 3.3 mmoles) at rt for 10 min. The aldehyde 2 (278 mg, 1.40 mmoles) was then added and the solution was stirred at rt for 4 h. The reaction mixture was partitioned between 1 N HCl and ethyl acetate. The organic layer was washed successively with water, saturated sodium carbonate and brine, then dried over sodium sulfate, filtered and concentrated. The crude was adsorbed on silica and purified on a silica gel column with a 5-10% ethyl acetate/hexanes gradient to afford ester 3 (258 mg, 59%). A solution of ester 3 (136 mg, 0.51 mmoles) in EtOH (5 ml) was placed in the Parr apparatus. A catalytic amount of 10% Pd/C (25 mg) was added and the mixture was shaken under an atmosphere of hydrogen (50 psi) for 1.5 h. The heterogeneous mixture was filtered through a cake of celite and concentrated to afford ester 4 (127 mg, 93%). This ester (127 mg, 0.47 mmoles) was dissolved in THF (10 ml)/ water (5 ml) and treated with lithium hydroxide monohydrate (197 mg, 4.7 mmoles) for 5 h at reflux. The mixture was cooled to rt and partitioned between 1N HCl and ethyl acetate. The organic layer was washed with water and brine then dried over sodium sulfate and concentrated to afford the desired acid (112 mg, 98%).
  • 27
  • [ 76279-46-4 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
88% With lithium aluminium tetrahydride In tetrahydrofuran at -20℃; for 0.75h; A solution of 2-phenoxybenzoic acid (660 mg, 3.08 mmoles) and N,O-dimethylhydroxylamine hydrochloride (451 mg, 4.62 mmoles) in DMF (15 ml) was treated at rt for 18 h with triethylamine (1.3 ml, 9.24 mmoles) and HBTU (1.75 g, 4.62 mmoles). The reaction mixture was partitioned between 1N NaOH and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford 1 which was not further purified (827 mg, 100%). A 1M solution of lithium aluminum hydride in THF (3.18 ml, 3.18 mmoles) was slowly added to a cold (-20° C.) solution of 1 (410 mg, 1.59 mmoles) in THF (8 ml). The solution was stirred at -20° C. for 45 min and then quenched slowly with water. The mixture was filtered through a cake of celite and the filtrate was partitioned between ethyl acetate and saturated bicarbonate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford aldehyde 2 (278 mg, 88%) which was not further purified. A solution of triethylphosphonoacetate (0.334 ml, 1.68 mmoles) in THF (2 ml) was treated with 60% sodium hydride (132 mg, 3.3 mmoles) at rt for 10 min. The aldehyde 2 (278 mg, 1.40 mmoles) was then added and the solution was stirred at rt for 4 h. The reaction mixture was partitioned between 1 N HCl and ethyl acetate. The organic layer was washed successively with water, saturated sodium carbonate and brine, then dried over sodium sulfate, filtered and concentrated. The crude was adsorbed on silica and purified on a silica gel column with a 5-10% ethyl acetate/hexanes gradient to afford ester 3 (258 mg, 59%). A solution of ester 3 (136 mg, 0.51 mmoles) in EtOH (5 ml) was placed in the Parr apparatus. A catalytic amount of 10% Pd/C (25 mg) was added and the mixture was shaken under an atmosphere of hydrogen (50 psi) for 1.5 h. The heterogeneous mixture was filtered through a cake of celite and concentrated to afford ester 4 (127 mg, 93%). This ester (127 mg, 0.47 mmoles) was dissolved in THF (10 ml)/ water (5 ml) and treated with lithium hydroxide monohydrate (197 mg, 4.7 mmoles) for 5 h at reflux. The mixture was cooled to rt and partitioned between 1N HCl and ethyl acetate. The organic layer was washed with water and brine then dried over sodium sulfate and concentrated to afford the desired acid (112 mg, 98%).
  • 28
  • [ 79-37-8 ]
  • [ 13807-84-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
7.65 g (83% over the two steps) With triethylamine In dichloromethane; dimethyl sulfoxide 40 N-(1-trans-(2-(2-phenoxyphenyl)cyclopropyl)methyl)-N-hydroxyurea To a solution of oxalyl chloride (6.82 g, 53.71 mmol) in CH2 Cl2 (250 mL) at -78° C., was added dimethylsulfoxide (8.76 g, 112.1 mmol) dropwise. The mixture was stirred for 5 mins. A solution of crude 2-phenoxybenzyl alcohol from above in CH2 Cl2 (20 mL) was added dropwise. Upon completion of addition, the reaction was stirred for 20 mins at -78° C. Triethylamine (23.58 g, 233.5 mmol) was then added dropwise. The cooling bath was removed and the reaction allowed to warm to room temperature. It was then diluted with brine (250 mL). The layers were separated and the aqueous was extracted with CH2 Cl2 (2*250 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 20:80) to afford 7.65 g (83% over the two steps) of 2-phenoxybenzaldehyde as a pale yellow oil.
7.65 g (83% over the two steps) With triethylamine In dichloromethane; dimethyl sulfoxide 40 N-(1-trans-(2-(2-phenoxyphenyl)cyclopropyl)methyl)-N-hydroxyurea To a solution of oxalyl chloride (6.82 g, 53.71 mmol) in CH2 Cl2 (250 mL) at -78° C., was added dimethylsulfoxide (8.76 g, 112.1 mmol) dropwise. The mixture was stirred for 5 mins. A solution of crude 2-phenoxybenzyl alcohol from above in CH2 Cl2 (20 mL) was added dropwise. Upon completion of addition, the reaction was stirred for 20 mins at -78∞C. Triethylamine (23.58 g, 233.5 mmol) was then added dropwise. The cooling bath was removed and the reaction allowed to warm to room temperature It was then diluted with brine (250 mL). The layers were separated and the aqueous was extracted with CH2 Cl2 (2*250 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 20:80) to afford 7.65 g (83% over the two steps) of 2-phenoxybenzaldehyde as a pale yellow oil.
  • 29
  • [ 2295-31-0 ]
  • [ 19434-34-5 ]
  • (5Z)-5-(2-phenoxybenzylidene)-1,3-thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With piperidine; acetic acid In toluene for 4h; Heating / reflux; 1.2 2-Phenoxybenzaldehyde (70 g; 0.353 mol) is diluted in 500 ml of toluene in a 100 mL round-bottomed flask on which is mounted Dean-Stark apparatus and a condenser. 2,4-Thiazolidinedione (41.4 g; 0.3533 mol), piperidine (10 mL) and acetic acid (10 mL) are then added. The reaction medium is refluxed for 4 hours. After cooling to room temperature, a precipitate forms, which is filtered off and then rinsed several times with toluene. The product obtained is dried under vacuum at 50° C. to give 100 g of a yellow solid (yield: 96%).
96% With piperidine; acetic acid In toluene for 4h; Heating / reflux; 1.2 2-Phenoxybenzaldehyde (70 g; 0.353 mol) is diluted in 500 mL of toluene in a 100 mL round-bottomed flask on which is mounted Dean-Stark apparatus and a condenser. 2,4-Thiazolidinedione (41.4 g; 0.3533 mol), piperidine (10 mL) and acetic acid (10 mL) are then added. The reaction medium is refluxed for 4 hours. After cooling to room temperature, a precipitate forms, which is filtered off and then rinsed several times with toluene. The product obtained is dried under vacuum at 50° C. to give 100 g of a yellow solid (yield: 96%).
  • 30
  • [ 75-11-6 ]
  • [ 19434-34-5 ]
  • [ 1030829-50-5 ]
YieldReaction ConditionsOperation in experiment
With methyllithium In tetrahydrofuran; diethyl ether at 20℃; Cooling with ice; 54.2 2) Production of 2-(2-phenoxyphenyl)ethanol To a solution of 2-phenoxybenzaldehyde (535 mg) in tetrahydrofuran (5 ml), 0.326 ml of diiodomethane and 5.4 ml of methyllithium (1.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes and then at room temperature for 1 hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in tetrahydrofuran (5 ml), 284 mg of sodium cyanoborohydride and 0.569 ml of trifluoroborane-diethyl ether complex were added under ice-cooling, and the reaction solution was stirred at the same temperature for 50 minutes. To the reaction solution was added a saturated saline solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50)) to afford the title compound as a colorless oil.
  • 31
  • [ 95-20-5 ]
  • [ 19434-34-5 ]
  • [ 62022-70-2 ]
YieldReaction ConditionsOperation in experiment
82% With iron(III) chloride hexahydrate In toluene at 50℃; for 1h; Inert atmosphere;
  • 32
  • [ 19434-34-5 ]
  • [ 100-66-3 ]
  • [ 19234-05-0 ]
YieldReaction ConditionsOperation in experiment
70% With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h;
  • 33
  • [ 19434-34-5 ]
  • [ 151-10-0 ]
  • [ 94866-88-3 ]
YieldReaction ConditionsOperation in experiment
69% With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h;
  • 34
  • [ 19434-34-5 ]
  • [ 108-95-2 ]
  • [ 77273-75-7 ]
YieldReaction ConditionsOperation in experiment
68% With scandium tris(trifluoromethanesulfonate) In dichloromethane at 50℃; for 24h;
  • 35
  • [ 552-89-6 ]
  • [ 98-80-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
52% With Wilkinson's catalyst; water; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;
  • 36
  • [ 19434-34-5 ]
  • [ 70-55-3 ]
  • [ 1304461-08-2 ]
YieldReaction ConditionsOperation in experiment
With copper diacetate In toluene Reflux; 2. Synthesis of substrates General procedure: 2-Phenylbenzaldehyde (1 mmol) and tosylamine 4 (1.2 mmol) were dissolved in 20 mL of toluene, and then the 10 mol % of Cu(OAc)2 was added as the catalyst. The resulting solution was raised to reflux and stirred overnight, and the progress of the reaction was monitored by TLC (EtOAc / petroleum ether = 1:7). Upon completion, the reaction mixture was poured into water (20 mL) and extracted with EtOAc (3 x 20 mL), and the combined organic layer was washed several times with brine. The solution was then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc / petroleum ether = 1:7) to obtain white solid product. Yield: 97%. Then the products were recrystallized from EtOAc and petroleum ether.
  • 37
  • [ 552-89-6 ]
  • [ 108-95-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
96% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere; Schlenk technique; Green chemistry; Heterogeneous copper-catalysed O-arylation of phenols by nitroarenes; general procedure General procedure: Under an argon atmosphere, a Schlenk tube was charged with MCM-41-2N-Cu(OAc)2(46 mg, 0.025 mmol), nitroarene 1 (0.5 mmol), phenol 2 (1.0 mmol), Cs2CO3 (1.0 mmol) and DMF (3 mL). The reaction mixture was stirred at 100 °C for 5 h under Ar. After being cooled to room temperature, the mixture was diluted with ethyl acetate (20 mL) and filtered. The MCM-41-2N-Cu(OAc)2 catalyst was washed with distilled water (2 × 5 mL), DMF (2 × 5 mL) and EtOH (2 × 5 mL) and could be reused in the next run. The filtrate was washed with water (2 × 10 mL) and dried over anhydrous MgSO4. After removal of the solvent under reduced pressure, the residue was purified by column chromatography (EtOAc/hexane) on silica gel to afford the desired product 3.
91% With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; Schlenk technique; 4.2 General procedure for the synthesis of unsymmetrical diaryl ethers General procedure: Under N2 atmosphere, a Schlenk tube was charged with nitroarenes 1 (0.5 mmol), phenols 2 (1.0 mmol), Cu(OAc)2·H2O (5 mol %), and Cs2CO3 (1.0 mmol) in DMF (3 mL) at room temperature. After that, the mixture was stirred constantly at 100 °C (oil bath temperature) for 4 h. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtrated. The filtrate was concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the desired arylated product 3.
75% With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;
33% With potassium phosphate; nickel dichloride In N,N-dimethyl-formamide at 100℃; for 4h;

  • 38
  • [ 90-02-8 ]
  • [ 108-95-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 4h;
  • 39
  • [ 19434-34-5 ]
  • [ 2065-66-9 ]
  • [ 46410-70-2 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: methyl-triphenylphosphonium iodide With potassium <i>tert</i>-butylate In tetrahydrofuran at -10℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: 2-(phenoxy)benzaldehyde In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;
  • 40
  • O-(quinuclidin-3-yl)hydroxylamine hydrogen chloride [ No CAS ]
  • [ 19434-34-5 ]
  • [ 1430841-79-4 ]
YieldReaction ConditionsOperation in experiment
68% With sodium carbonate In methanol at 20℃; for 3h; Inert atmosphere; 2.1 4.1.2.1 Representative procedure for synthesis of O-quinuclidin-3-yl oxime (1) General procedure: To a solution of O-(quinuclidin-3-yl)hydroxylamine hydrogen chloride 4 (642 mg, 2.98 mmol) in methanol (30 mL) were added 2-(benzyloxy)benzaldehyde (949 mg, 4.47 mmol) and Na2CO3 (474 mg, 4.47 mmol). The reaction mixture was stirred at room temperature for 3 h, quenched with water (25 mL) and extracted with chloroform (3 × 30 mL). The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (CHCl3/MeOH = 10:1) to give the title compound 1 (924 mg, 92%) as a solid.
  • 41
  • [ 19434-34-5 ]
  • [ 57260-71-6 ]
  • [ 1460028-56-1 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; 35 Example 35: 2,5-Dioxopyrrolidin-l-yl 4-[(2-phenoxyphenyl)methyl]piperazine-l- carboxylate Example 35: 2,5-Dioxopyrrolidin-l-yl 4-[(2-phenoxyphenyl)methyl]piperazine-l- carboxylate [00165] To a stirring solution of 2-phenoxybenzaldehyde (297 mg, 1.50 mmol, 1.0 equiv) and tert-butyl piperazine-1 -carboxylate (307 mg, 1.65 mmol, 1.1 equiv) in CH2CI2 (10 mL) was added NaBH(OAc)3 (477 mg, 2.25 mmol, 1.5 equiv). The reaction was stirred for 2 h at room temperature and subsequently quenched upon addition of aqueous NaOH (10 mL, 1.0 M). The biphasic mixture was vigorously stirred for 30 min and poured into a separatory funnel containing brine (50 mL). The product was extracted with CH2CI2 (50 mL, 3x), and the combined organic layers were dried over anhydrous MgS04 and concentrated under reduced pressure to provide a crude colorless oil, which was used in subsequent steps without further purification.
  • 42
  • [ 540-38-5 ]
  • [ 446-52-6 ]
  • [ 262444-19-9 ]
  • [ 533-58-4 ]
  • 2-iodophenyl 2-formylphenyl ether [ No CAS ]
  • [ 19434-34-5 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In neat (no solvent) at 140℃; for 2h; Microwave irradiation; 3.2. General Procedure for O-Arylation of Iodophenolswith 2-Fluorobenzaldehyde under MW Conditions General procedure: A mixture of 0.22 g (1.0 mmol) of 2-, 3- or 4-iodophenol, 0.11 mL (1.1 mmol) of 2-fluorobenzaldehyde, 0.14 g (1.0mmol) of potassium carbonate and in certain cases 11.4 mg(0.050 mmol) of TEBAC in a closed vial was irradiated in a CEM Discover microwave reactor at 120-140 °C for 2 hours. The reaction mixture was taken up in 25 mL of ethyl acetate and the suspension was filtered. Evaporation of the volatile components provided the crude product that was passed through a thin (ca. 2-3 cm) layer of silica gel using ethylacetate as the eluant to give an oil that was analysed by GC-MS or GC. Similar reactions were carried out in 3 mL of acetonitrileor N,N-dimethylformamide as the solvent. The work-up was similar to that described for the solvent-free alkylationsabove, but in this case, ethyl acetate did not have to beadded. The major components of the above reactions, such ascompounds 2, 3 and 8 were obtained in a pure form byrepeated chromatography as above, but using longercolumns. In a few cases, control experiments were performed in asimilar way under conventional heating.
With potassium carbonate In acetonitrile at 120℃; for 2h; Microwave irradiation; 3.2. General Procedure for O-Arylation of Iodophenolswith 2-Fluorobenzaldehyde under MW Conditions General procedure: A mixture of 0.22 g (1.0 mmol) of 2-, 3- or 4-iodophenol, 0.11 mL (1.1 mmol) of 2-fluorobenzaldehyde, 0.14 g (1.0mmol) of potassium carbonate and in certain cases 11.4 mg(0.050 mmol) of TEBAC in a closed vial was irradiated in a CEM Discover microwave reactor at 120-140 °C for 2 hours. The reaction mixture was taken up in 25 mL of ethyl acetate and the suspension was filtered. Evaporation of the volatile components provided the crude product that was passed through a thin (ca. 2-3 cm) layer of silica gel using ethylacetate as the eluant to give an oil that was analysed by GC-MS or GC. Similar reactions were carried out in 3 mL of acetonitrileor N,N-dimethylformamide as the solvent. The work-up was similar to that described for the solvent-free alkylationsabove, but in this case, ethyl acetate did not have to beadded. The major components of the above reactions, such ascompounds 2, 3 and 8 were obtained in a pure form byrepeated chromatography as above, but using longercolumns. In a few cases, control experiments were performed in asimilar way under conventional heating.
  • 43
  • [ 540-38-5 ]
  • [ 446-52-6 ]
  • [ 262444-19-9 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Microwave irradiation; 3.2. General Procedure for O-Arylation of Iodophenolswith 2-Fluorobenzaldehyde under MW Conditions General procedure: A mixture of 0.22 g (1.0 mmol) of 2-, 3- or 4-iodophenol, 0.11 mL (1.1 mmol) of 2-fluorobenzaldehyde, 0.14 g (1.0mmol) of potassium carbonate and in certain cases 11.4 mg(0.050 mmol) of TEBAC in a closed vial was irradiated in a CEM Discover microwave reactor at 120-140 °C for 2 hours. The reaction mixture was taken up in 25 mL of ethyl acetateand the suspension was filtered. Evaporation of the volatile components provided the crude product that was passed through a thin (ca. 2-3 cm) layer of silica gel using ethylacetate as the eluant to give an oil that was analysed by GC-MS or GC. Similar reactions were carried out in 3 mL of acetonitrileor N,N-dimethylformamide as the solvent. The work-up was similar to that described for the solvent-free alkylationsabove, but in this case, ethyl acetate did not have to beadded. The major components of the above reactions, such ascompounds 2, 3 and 8 were obtained in a pure form byrepeated chromatography as above, but using longercolumns. In a few cases, control experiments were performed in asimilar way under conventional heating.
  • 44
  • [ 540-38-5 ]
  • [ 446-52-6 ]
  • [ 262444-19-9 ]
  • [ 533-58-4 ]
  • [ 19434-34-5 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In neat (no solvent) at 120℃; for 2h; Microwave irradiation; 3.2. General Procedure for O-Arylation of Iodophenolswith 2-Fluorobenzaldehyde under MW Conditions General procedure: A mixture of 0.22 g (1.0 mmol) of 2-, 3- or 4-iodophenol, 0.11 mL (1.1 mmol) of 2-fluorobenzaldehyde, 0.14 g (1.0mmol) of potassium carbonate and in certain cases 11.4 mg(0.050 mmol) of TEBAC in a closed vial was irradiated in a CEM Discover microwave reactor at 120-140 °C for 2 hours. The reaction mixture was taken up in 25 mL of ethyl acetate and the suspension was filtered. Evaporation of the volatile components provided the crude product that was passed through a thin (ca. 2-3 cm) layer of silica gel using ethylacetate as the eluant to give an oil that was analysed by GC-MS or GC. Similar reactions were carried out in 3 mL of acetonitrileor N,N-dimethylformamide as the solvent. The work-up was similar to that described for the solvent-free alkylationsabove, but in this case, ethyl acetate did not have to beadded. The major components of the above reactions, such ascompounds 2, 3 and 8 were obtained in a pure form byrepeated chromatography as above, but using longercolumns. In a few cases, control experiments were performed in asimilar way under conventional heating.
  • 45
  • [ 533-58-4 ]
  • [ 446-52-6 ]
  • 2-iodophenyl 2-formylphenyl ether [ No CAS ]
  • [ 19434-34-5 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In neat (no solvent) at 120℃; for 2h; Microwave irradiation; 3.2. General Procedure for O-Arylation of Iodophenolswith 2-Fluorobenzaldehyde under MW Conditions General procedure: A mixture of 0.22 g (1.0 mmol) of 2-, 3- or 4-iodophenol, 0.11 mL (1.1 mmol) of 2-fluorobenzaldehyde, 0.14 g (1.0mmol) of potassium carbonate and in certain cases 11.4 mg(0.050 mmol) of TEBAC in a closed vial was irradiated in a CEM Discover microwave reactor at 120-140 °C for 2 hours. The reaction mixture was taken up in 25 mL of ethyl acetate and the suspension was filtered. Evaporation of the volatile components provided the crude product that was passed through a thin (ca. 2-3 cm) layer of silica gel using ethylacetate as the eluant to give an oil that was analysed by GC-MS or GC. Similar reactions were carried out in 3 mL of acetonitrileor N,N-dimethylformamide as the solvent. The work-up was similar to that described for the solvent-free alkylationsabove, but in this case, ethyl acetate did not have to beadded. The major components of the above reactions, such ascompounds 2, 3 and 8 were obtained in a pure form byrepeated chromatography as above, but using longercolumns. In a few cases, control experiments were performed in asimilar way under conventional heating.
  • 46
  • [ 19434-34-5 ]
  • [ 108-67-8 ]
  • [ 29903-61-5 ]
YieldReaction ConditionsOperation in experiment
88% With trifluorormethanesulfonic acid; acetic anhydride In 1,2-dichloro-ethane at 20℃; Green chemistry;
  • 47
  • [ 773837-37-9 ]
  • [ 19434-34-5 ]
  • 2-amino-2-(2-phenoxyphenyl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With ammonium hydroxide; ammonium chloride In methanol; water; ethyl acetate at 0 - 20℃; for 4h; 85.a Example 85a
2-amino-2-(2-phenoxyphenyl)acetonitrile Example 85a 2-amino-2-(2-phenoxyphenyl)acetonitrile A solution of 2-phenoxybenzaldehyde (1.0 g, 5.04 mmol) in methanol (10 mL) was added to a solution of sodium cyanide (0.297 g, 6.05 mmol) and ammonium chloride (0.494 g, 9.23 mmol) in ammonium hydroxide (10 mL, 85 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated by rotary evaporation. The residue was taken up in water and extracted with dichloromethane (2*). The combined organics were washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes) to provide the title compound (1.065 g, 94% yield).
  • 48
  • [ 66003-76-7 ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; N,N-dimethyl-formamide With potassium fluoride at 20 - 60℃; for 0.05h; Inert atmosphere; Schlenk technique; Stage #2: Diphenyliodonium triflate at 60℃; for 3h; Inert atmosphere; Schlenk technique; chemoselective reaction;
  • 49
  • [ 58109-40-3 ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
83% With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 3h; chemoselective reaction;
  • 50
  • [ 62613-15-4 ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
69% With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 3h; chemoselective reaction;
  • 51
  • diphenyliodonium nitrate [ No CAS ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
71% With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 3h; chemoselective reaction;
  • 52
  • [ 1483-72-3 ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium fluoride In N,N-dimethyl-formamide at 60℃; for 3h;
  • 53
  • [ 1483-73-4 ]
  • [ 88284-48-4 ]
  • [ 68-12-2 ]
  • [ 19434-34-5 ]
  • 54
  • [ 19434-34-5 ]
  • 2-hydroxy-6-phenoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 100℃; for 8h; Schlenk technique; Inert atmosphere; chemoselective reaction;
  • 55
  • [ 501-30-4 ]
  • [ 19434-34-5 ]
  • [ 126-81-8 ]
  • 2‐(hydroxymethyl)‐7, 7‐dimethyl‐10‐(2‐phenoxyphenyl)‐7, 8‐dihydropyrano[3, 2‐b]chromene‐4, 9(6H, 10H)‐dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 1-deoxy-1-(methylamino)-D-glucitol In ethanol; water at 20℃; for 0.116667h;
88% With ytterbium perfluorooctanoate In neat (no solvent) at 80℃; for 0.1h; Microwave irradiation; Green chemistry;
  • 56
  • [ 66003-76-7 ]
  • [ 71730-46-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
62% With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 60℃; for 0.5h; Schlenk technique; Sealed tube;
  • 57
  • [ 58109-40-3 ]
  • [ 71730-46-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
61% With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 60℃; for 0.5h; Schlenk technique; Sealed tube;
  • 58
  • [ 6293-66-9 ]
  • [ 71730-46-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
55% With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 60℃; for 0.5h; Schlenk technique; Sealed tube;
  • 59
  • diphenyliodonium tetrafluoroborate [ No CAS ]
  • [ 71730-46-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
59% With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 60℃; for 0.5h; Schlenk technique; Sealed tube;
  • 60
  • [ 5927-18-4 ]
  • [ 19434-34-5 ]
  • methyl 3-(2-phenoxyphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: trimethyl phosphonoacetate With n-butyllithium In tetrahydrofuran at -80℃; for 1h; Stage #2: 2-(phenoxy)benzaldehyde In tetrahydrofuran at 20℃; 10 Methyl 3-(2-phenoxyphenyl)acrylate (26b) Methyl 3-(2-phenoxyphenyl)acrylate (26b) n-BuLi (30.6 ml, 76 mmol) was added dropwise over 10 minutes to a cooled solution (-80 °C) of methyl 2-(dimethoxyphosphoryl)acetate (11.04 mL, 76 mmol) in THF (100 mL) and the resulting mixture was stirred for 1 h. Then 2-phenoxybenzaldehyde (26a, 7.57 g, 38.2 mmol) was added, the reaction mixture was slowly warmed up to rt and stirred overnight. Upon completion the mixture was concentrated in vacuo, saturated NaHCO3 (80 mL) was added and product was extracted using EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried, concentrated in vacuo and purified by flash chromatography to yield methyl 3-(2-phenoxyphenyl)acrylate (6.6 g, 26.0 mmol, 68%). 1H NMR (CDCl3, 400 MHz): δ 8.03 (d, J = 16.2 Hz, 1 H), 7.62 (dd, J = 7.8, 1.7 Hz, 1 H), 7.39 -6.81 (m, 8H), 6.57 (d, J = 16.2, 1 H), 3.79 (s, 3H).
  • 61
  • [ 19434-34-5 ]
  • [ 1021-25-6 ]
  • 8-(2-phenoxybenzyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(phenoxy)benzaldehyde; 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; chloroform 19.B Step B Step B: To a mixture of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (291 mg, 1.26 mmol) and 2-phenoxybenzaldehyde (299 mg , 1.50 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (454 mg, 2.14 mmol). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 20h. The reaction mixture was then quenched with 1 N aqueous NaHCO3 and extracted with CHCl3 (100 mL). The combined extracts were dried over Na2SO4, filtered and concentrated. The isolated solid was purified by flash chromatography on silica gel to yield the title compound as a free base. The free base was dissolved in CHCl3 (35 mL), and treated with 2.5 mL of 1N HCl in Et2O. The corresponding HCl salt was precipitated by addition of Et2O, then collected by filtration and dried the vacuum oven at 50 °C for 18h to yield the title product as an amorphous solid. MS (loop pos): MH+= 414.1 (100%). 1H NMR (300 MHz, DMSO d6) δ□1.85-1.95 (m, 1 H), 2.90-3.10 (m, 2H), 3.35-3.60 (m, 2H), 3.70-3.85 (m, 2H), 4.35-4.45 (m, 2H), 4.60 (s, 2H), 7.05-7.20 (m, 4H), 7.25-7.35 (m, 4H, 7.45-7.55 (m, 3H), 7.85-7.90 (m, 1 H), 9.00 (s, 1 H), 10.9 (s, 1 H)
  • 62
  • [ 19434-34-5 ]
  • [ 141-78-6 ]
  • C17H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In 1,2-dichloro-ethane at 50℃; Inert atmosphere; 3.1 (1) Preparation of 3-o-phenoxyphenyl-2-enyl ester: In a 500 ml four-necked flask equipped with a condenser,Under nitrogen atmosphere followed by adding 200mL of dichloroethane,0.25 mol sulfuric acid (concentration 98%),50 ° C dropwise0.5 mol 3-o-phenoxy-benzaldehyde and0.6 mol ethyl acetate mixture,Within 2-4 hours the above mixture was added dropwise,And then incubated to the material in the formaldehyde aldehyde 3-o-phenoxy-benzaldehyde gas spectrum containing normalizedAmount 85%.Solvent recovery by recycling, recovery 80%;
  • 63
  • [ 19434-34-5 ]
  • C26H22O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With indium(III) triflate; triethylsilane In neat (no solvent) at 35℃; for 0.0833333h; Experimental procedure for the dibenzyl ether synthesis In(OTf)3 (8.4 mg, 0.015 mmol) was added to a stirred mixture of 2-phenoxybenzaldehyde 1a (60 mg, 0.30 mmol) and Et3SiH (87 mg, 0.75 mmol) in a round bottomed flask (10 mL) at room temperature (35 °C). The reaction mixture was stirred for 5 min and quenched with aq. NH4Cl solution (1 mL). Then the mixture was extracted with ethyl acetate (50 mL) and washed with brine (1 x 10 mL), dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica-gel column chromatography using 1 % ethyl acetate in hexanes as eluent toobtain dibenzyl ether 4a (53 mg, 92 % yield) as a colorless oil. Compound 4a: colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.53 (d, J = 7.8 Hz, 2H), 7.32-7.19 (m, 6H), 7.15-7.02 (m, 4H), 6.94-6.85 (m, 6H), 4.65 (s, 2H); HRMS (ESI) calculated for C26H22NaO3: 405.1467 found 405.1440.
Multi-step reaction with 2 steps 1: triethylsilane; scandium tris(trifluoromethanesulfonate) / dichloromethane / 2 h / Reflux 2: indium(III) triflate; triethylsilane / 1,2-dichloro-ethane / 3 h / 60 °C
  • 64
  • [ 91-63-4 ]
  • [ 19434-34-5 ]
  • 1-(2-phenoxyphenyl)-2-(quinolin-2-yl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With acetic acid In water at 100℃; for 24h;
81% With acetic acid In water at 100℃; for 24h; 1-2 General procedure: Using 2-methylquinoline and 2-phenoxybenzaldehyde as raw materials, the acid, solvent and reaction temperature are shown in Table 1. The reaction was carried out in a 25mL reaction tube for 24h, then cooled to room temperature, and an appropriate amount of water was added and used. The organic phase was collected three times by extraction with ethyl acetate, and the solvent was removed by rotary evaporation under reduced pressure using a rotary evaporator, and the product was separated and purified through a thin-layer plate to obtain the product. The thin-layer plate developer used was (5-30) in volume ratio: 1 petroleum ether: ethyl acetate mixed solvent.
  • 65
  • [ 91-63-4 ]
  • [ 19434-34-5 ]
  • (E)-2-(2-phenoxystyryl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 66
  • [ 1198-37-4 ]
  • [ 19434-34-5 ]
  • 2-(4-methylquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
  • 67
  • [ 19434-34-5 ]
  • [ 4295-06-1 ]
  • 2-(4-chloroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With acetic acid In water at 100℃; for 24h;
  • 68
  • [ 877-43-0 ]
  • [ 19434-34-5 ]
  • 2-(6-methylquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid In water at 100℃; for 24h;
  • 69
  • [ 877-43-0 ]
  • [ 19434-34-5 ]
  • (E)-6-methyl-2-(2-phenoxystyryl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 70
  • [ 1128-61-6 ]
  • [ 19434-34-5 ]
  • (E)-6-fluoro-2-(2-phenoxystyryl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 71
  • [ 1128-61-6 ]
  • [ 19434-34-5 ]
  • 2-(6-fluoroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With acetic acid In water at 100℃; for 24h;
63% With acetic acid In water at 100℃; for 24h; 3 Example 2 General procedure: The reaction was performed under the above optimal reaction conditions, and different reaction materials were replaced. The specific reaction materials are shown in Table 2. The amount of substituted 2-methylquinoline was 0.45 mmol, and the amount of substituted benzaldehyde was 0.3 mmol. The amount of acetic acid was 0.06 mmol and the amount of water was 1.5 mL. The reaction was carried out in a 25 mL reaction tube at a reaction temperature of 100 ° C for 24 hours. Then the heating and stirring were stopped. After cooling to room temperature, an appropriate amount of water was added and ethyl acetate was used. The organic phase was collected three times by extraction, and the solvent was removed by rotary evaporation under reduced pressure. The product was separated and purified through a thin-layer plate. The thin-layer plate developer used was petroleum ether: ethyl acetate with a volume ratio of (5-30): 1. The solvents were mixed to prepare hydroxyquinoline compounds with different substituents.
  • 72
  • [ 92-46-6 ]
  • [ 19434-34-5 ]
  • (E)-6-chloro-2-(2-phenoxystyryl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 73
  • [ 92-46-6 ]
  • [ 19434-34-5 ]
  • 2-(6-chloroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With acetic acid In water at 100℃; for 24h;
  • 74
  • [ 877-42-9 ]
  • [ 19434-34-5 ]
  • (E)-6-bromo-2-(2-phenoxystyryl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 75
  • [ 877-42-9 ]
  • [ 19434-34-5 ]
  • 2-(6-bromoquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid In water at 100℃; for 24h;
  • 76
  • [ 19434-34-5 ]
  • [ 1078-28-0 ]
  • 2-(6-methoxyquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
  • 77
  • [ 6628-28-0 ]
  • [ 19434-34-5 ]
  • 2-(6-ethoxyquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With acetic acid In water at 100℃; for 24h;
  • 78
  • [ 1128-74-1 ]
  • [ 19434-34-5 ]
  • 2-(7-fluoroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
  • 79
  • [ 4965-33-7 ]
  • [ 19434-34-5 ]
  • 2-(7-chloroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With acetic acid In water at 100℃; for 24h;
  • 80
  • [ 3033-82-7 ]
  • [ 19434-34-5 ]
  • 2-(8-chloroquinolin-2-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
  • 81
  • [ 1721-93-3 ]
  • [ 19434-34-5 ]
  • 2-(isoquinolin-1-yl)-1-(2-phenoxyphenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With acetic acid In water at 100℃; for 24h;
  • 82
  • [ 1721-93-3 ]
  • [ 19434-34-5 ]
  • (E)-1-(2-phenoxystyryl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With 1,3-dimethylbarbituric acid; acetic acid In water at 100℃; for 24h;
  • 83
  • [ 504-29-0 ]
  • [ 19434-34-5 ]
  • N-(2-phenoxybenzyl)pyridine-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.6 g Stage #1: 2-aminopyridine; 2-(phenoxy)benzaldehyde In dichloromethane at 20℃; for 0.5h; Stage #2: In tetrahydrofuran 1.2 Step 2: Synthesis of N- (2-phenoxybenzyl) pyridine-2-amine Add 2- (phenoxy) benzaldehyde (1.98g, 10mmol), o-aminopyridine (0.94g, 10mmol)And dichloromethane (20mL) were added to a 50mL single-necked flask, and stirred at room temperature for 30min.The reaction solution was concentrated under reduced pressure, filtered, and the residual solution was reacted under vacuum at 90 ° C for 1 h;Then drop to room temperature, add 20mL of dichloromethane, and stir at room temperature for 30min.The reaction solution was concentrated under reduced pressure, filtered, and the residual solution was reacted under vacuum at 90 ° C for 1 h.If it is repeated three times,2.6 g of a yellow solid was obtained.The above yellow solid was dissolved in tetrahydrofuran (20 mL) and slowly added dropwise to a mixed solution of sodium borohydride (304 mg, 8.0 mmol) in a tetrahydrofuran / methanol (129 mL, v / v = 5/124); , Stir for 12h at room temperature,20 mL of water was added to quench the reaction, and ethyl acetate (30 mL x 3) was added to extract the reaction solution.The organic phases were combined, dried over anhydrous sodium sulfate for 1 h, filtered, and concentrated under reduced pressure.The residue was separated by silica gel column chromatography [petroleum ether / ethyl acetate (v / v) = 7: 3],The title compound was obtained (light yellow oil, 1.8 g, yield: 65%).
  • 84
  • 2-(2-phenoxyphenyl)-1,3-oxathiolane [ No CAS ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
90% With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;
  • 85
  • potassium 4-methyl-1-phenyl-2,6,7-trioxa-1-borabicyclo-[2.2.2]octan-1-uide [ No CAS ]
  • [ 552-89-6 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
86% With copper (II)-fluoride; Oxone; caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; 7 Example 7 At room temperature, add the aromatic heterocyclic borate compound 1a of the above formula to the reaction flask o-nitrobenzaldehyde compound 2b, catalyst CuF2, additive Oxone, basic compound Cs2CO3, reaction solvent DMSO.Among them, the molar ratio of 1a to 2b is 1:2, the molar ratio of 1a to catalyst CuF2 is 1:0.05, and the molar ratio of 1a to additive Oxone is 1:1,The molar ratio of 1a to base Cs2CO3 is 1:2.5, and the molar ratio of 1a to the reaction organic solvent is about 1:100 (or about 1:150),Stir and heat to 100°C under air conditions, and react for 24 hours.After the reaction was completed, water was added to quench the reaction, the crude product was extracted with ether, and the organic layers were combined.Anhydrous Na2SO4 was dried and evaporated to dryness under reduced pressure. After separation and purification, the corresponding product 3g was obtained with a yield of 82% (1a:DMSO≈1:100) or 86% (1a:DMSO≈1:150).
  • 86
  • [ 19434-34-5 ]
  • [ 100-19-6 ]
  • (E)-1-(4-nitro-phenyl)-3-(2-phenoxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With piperidine; acetic acid In benzene for 14h; Reflux; Experimental procedure for the synthesis of enones: General procedure: A mixture of aldehyde (305 mg, 1.0 mmol), 4-acetylbenzonitrile (145 mg, 1.0 mmol), piperidine (17 mg, 0.20 mmol), acetic acid (24 mg, 0.40 mmol) in benzene was heated under reflux for 14 h. The reaction mixture was then cooled to room temperature and solvent evaporated. The residue was diluted with brine (25 mL) and extracted with ethyl acetate (3 x 25 mL), dried over Na 2 SO 4 and evaporated. The crude reaction mixture was purified by short silica gel column chromatography using 2→5% gradient mixture of ethyl acetate in hexanes as eluent to obtain (E)-4-(3-(2-(4-isopropyl-3-methylphenoxy)quinolin-3-yl)acryloyl)benzonitrile E (294 mg, 68%) as light brown viscous oil.
  • 87
  • [ 19434-34-5 ]
  • [ 99-91-2 ]
  • C21H15ClO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; acetic acid In benzene for 14h; Reflux; Experimental procedure for the synthesis of enones: General procedure: A mixture of aldehyde (305 mg, 1.0 mmol), 4-acetylbenzonitrile (145 mg, 1.0 mmol), piperidine (17 mg, 0.20 mmol), acetic acid (24 mg, 0.40 mmol) in benzene was heated under reflux for 14 h. The reaction mixture was then cooled to room temperature and solvent evaporated. The residue was diluted with brine (25 mL) and extracted with ethyl acetate (3 x 25 mL), dried over Na 2 SO 4 and evaporated. The crude reaction mixture was purified by short silica gel column chromatography using 2→5% gradient mixture of ethyl acetate in hexanes as eluent to obtain (E)-4-(3-(2-(4-isopropyl-3-methylphenoxy)quinolin-3-yl)acryloyl)benzonitrile E (294 mg, 68%) as light brown viscous oil.
  • 88
  • [ 19434-34-5 ]
  • [ 92-83-1 ]
YieldReaction ConditionsOperation in experiment
86% With indium(III) triflate In di-isopropyl ether at 95℃; for 24h; Inert atmosphere; Sealed tube;
85% With titanium tetrachloride In dichloromethane at 20℃; for 24h;
  • 89
  • [ 19434-34-5 ]
  • C13H11O5S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium metabisulfite In ethanol; water 2.1.1.4. General synthesis of sodium metabisulfite adduct ofsubstituted aldehydes General procedure: Related substituted aldehydes (30 mmol)were dissolved in EtOH (100 mL) and sodium metabisulfite (3.2 g)(in 5 mL of water) was added in portions. The reaction mixture wasstirred vigorously. The mixture was kept in a refrigerator for awhile. The white precipitate was gained by filtration, dried and used for the further steps without purification and characterisation
  • 90
  • [ 46410-70-2 ]
  • [ 19434-34-5 ]
YieldReaction ConditionsOperation in experiment
70 %Chromat. With oxygen; potassium carbonate In methanol at 130℃; for 12h; Sealed tube; Autoclave; 20 Example 20 Add Co-N-C (5 mol% relative to the substrate), 2-phenoxy-styrene (1 mmol), K2CO3 (20 mol%), and 4 mL methanol into a 25 mL polytetrafluoroethylene-lined autoclave, Seal the reactor, fill it with oxygen pressure to 0.4MPa, put the reactor in an oil bath at 130°C, stir and react for 12h at 400 rpm, After the reaction, the reactor was cooled to room temperature, the reactor was opened, and the internal standard biphenyl (60mg) was added. The qualitative products were detected by gas chromatography-mass spectrometry, and the yields of the substrate 2-phenoxy-styrene and the product benzaldehyde were quantified by gas chromatography internal standard method in Table 1.
  • 91
  • [ 5256-74-6 ]
  • [ 19434-34-5 ]
  • [ 512197-88-5 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In methanol at 20℃; for 3h;
  • 92
  • [ 19434-34-5 ]
  • [ 67-64-1 ]
  • C16H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;
  • 93
  • [ 19434-34-5 ]
  • [ 67-64-1 ]
  • C16H16O3 [ No CAS ]
  • C16H14O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 90% With potassium hydroxide In methanol at 20℃; for 5h;
1: 78% 2: 10% With potassium carbonate In methanol at 20℃; for 5h;
  • 94
  • [ 19434-34-5 ]
  • [ 81290-20-2 ]
  • C14H10F2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine In 1,4-dioxane; N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Sealed tube; Difluoromethylenation of Aldehydes and Ketones to 1,1-Difluoroalkenes;15 General Procedure General procedure: A pressure vessel charged with a stir bar, PPh3 (1.5 equiv), LiI (1.0equiv), and solid aldehyde (5.49 mmol, 1.0 equiv) (liquid aldehydewas introduced using a syringe) was sealed under inert atmosphere(argon). To this vial, anhyd 1,4-dioxane (15 mL) and anhyd DMF (2mL) were injected. Finally, TMSCF3 (13.72 mmol, 2.5 equiv) was addedthrough a syringe. The resulting mixture was heated at 120 °C for 24h. As the reaction proceeded, the reaction mixture turned from paleorange to dark brown. The reaction vial was cooled down to rt, thenMeI (4-5 equiv) was added and stirred for 5 min to prevent PPh3 interferenceduring the column chromatography separation (31P NMRconfirmed the absence of phosphine). The reaction mixture wasquenched with H2O (5 mL) and extracted with Et2O (3 × 5 mL). Thecombined Et2O layers were dried (anhyd MgSO4), filtered and evaporatedon a rotary evaporator. The crude product obtained was purifiedby silica gel column chromatography eluting with pentane orhexane or hexane/EtOAc gradient. The pure fractions were combinedand the solvent was evaporated to obtain the pure 1,1-difluoroolefin.In the case of a volatile product, it was isolated by distillation underreduced pressure.Spectroscopic data were consistent with the earlier reported information.15
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