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CAS No. : | 1515-95-3 | MDL No. : | MFCD00015176 |
Formula : | C9H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HDNRAPAFJLXKBV-UHFFFAOYSA-N |
M.W : | 136.19 | Pubchem ID : | 73690 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.71 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.94 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 3.09 |
Log Po/w (WLOGP) : | 2.26 |
Log Po/w (MLOGP) : | 2.46 |
Log Po/w (SILICOS-IT) : | 2.63 |
Consensus Log Po/w : | 2.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.94 |
Solubility : | 0.155 mg/ml ; 0.00114 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.95 |
Solubility : | 0.152 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.29 |
Solubility : | 0.0705 mg/ml ; 0.000518 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P210-P264-P270-P280-P301+P312-P330-P370+P378-P403+P235-P501 | UN#: | |
Hazard Statements: | H302-H227 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; oxalic acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; water; | EMBODIMENT 3 4-Ethyl-3-cyclohexen-1-one To a stirred refluxing mixture of 600 ml of dry ether and 1600 ml of liquid ammonia was added 136 g of <strong>[1515-95-3]p-ethylanisole</strong>. After 15 minutes, there was added portionwise, at -35 to -32 C., a 26.4 g quantity of lithium ribbon over 0.5-1 hour. After an additional 15 minutes, 193 g of dry ethanol was added dropwise at -35 to -32 C. Stirring was continued until the blue color disappeared, and the ammonia was allowed to evaporate on standing overnight. The residue was poured into 1 l of ice water and extracted twice with ether. The combined ether extracts concentrated to a volume of about 300 ml was stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature. This mixture was diluted with 1 liter of water and extracted twice with ether. The combined ether extracts were washed with 5% sodium bicarbonate and then with water. After drying, the ether solution was vacuum-concentrated to a residue of 104.4 g of desired product; it was 94% pure by GLC analysis and used without distillation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 60℃; under 60006 Torr; for 166h;Autoclave; Schlenk technique; | General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC. | |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100℃; under 60006 Torr; for 25h;Autoclave; Schlenk technique; | General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With hydrogen; In methanol; at 20℃; for 24h; | General procedure: The mixture of the substrate (0.250 mmol), 0.5% Pd/MS3A or 0.5% Pd/MS5A (10 wt % of the substrate) and MeOH (1 mL) was stirred under H2 atmosphere (balloon) at room temperature. After a given period, the reaction mixture was filtered through a membrane filter (Millipore, Millex-LH, 0.45 mm), and the filtrate was concentrated in vacuo to produce the corresponding reduced product. |
With hydrogen; In neat (no solvent); at 40℃; under 7600.51 Torr; for 2h;Autoclave;Catalytic behavior; | General procedure: In a typical hydrogenation reaction, 0.005 g PdCHT was addedto 0.1 g substrate in a reaction glass vial fitted with a magneticstirring bar and a septum cap. The reaction vial was then placedinto a 300 mL steel Parr autoclave. The autoclave was flushed withhydrogen three times to remove air inside the autoclave and finallypressurized to 10 atm, which was kept at 40C oil bath. After thereaction, the autoclave was placed into a water bath and cooled toroom temperature. Finally, the remaining hydrogen was carefullydischarged and the products were analyzed by a GC instrument. | |
100%Chromat. | With water; aluminium; at 60℃; for 6h; | General procedure: The mixture of a substrate (20 mg, 0.20 mmol)(Wako), Raney Ni-Al alloy (500 wt%), Al powder (500 wt%) (53-150 mum, 99.5%) (Wako) and Pt/C, Pd/C, Ru/C orRh/C (20 mg) (4.5 mole % metal) was added to water (0.5 mL) (Wako distilled water). After heating themixture at 60-120 oC for 6-12 h, it was cooled to room temperature. The solution was then diluted with 1 mLwater and stirred overnight at room temperature in a sealed tube. After 24 h, the solution was extracted withdiethyl ether (3 × 2 mL) as per the reported procedure.37 The combined organic layers were dried overanhydrous MgSO4 and filtered through a porous cotton plug followed by concentrating in vacuum to afford thecorresponding reduction product. The yields were determined by GLC analysis using the standard compound(1,2,3,4-tetrahydronaphthalene), and the products were identified by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With C20H26B10Cl2FeN6; dihydrogen peroxide; In methanol; at 20℃; for 8h; | Dissolve 2-methylethylbenzene (1.0 mmol), iron complex 1 (0.02 mmol) and H2O2 (1.5 mmol) in 2 mL of methanol and react at room temperature for 8 hours.After the reaction, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding product C9H12O was obtained (93% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver(II) sulfate; iodine; In methanol; at 20℃; | A mixture of silver sulfate (1.15 g, 3.68 mmol) and iodine (0.93 g, 3.68 mmol) were stirred in methanol at room temperature. A solution of <strong>[1515-95-3]p-ethylanisole</strong> (0.50 g, 3.68 mmol) in methanol was added dropwise to the stirring mixture. The mixture was stirred at room temperature until completion of the reaction. It was filtered and the filtrate was concentrated. The residue was dissolved in methylene chloride, washed with 1 N sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained without further purification. ¹H NMR (CDCl3,500 MHz) No. 7.64 (d, J = 2.0 Hz, 1H), 7.15 (dd, J = 8.5,2.0 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 3.88 (s, 3H), 2.58 (q, J = 15.5, 8.0 Hz, 2H), 1.23 (t, J = 7.5 Hz, 3H). Step B: 2-(5-Ethyl-2-methoxy(at)henyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane To a mixture of bispinacolatodiboron (0.70 g, 2.95 mmol), potassium acetate (0.67 g, 6.81 mmol) and dichlor[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (55 mg, 0.068 mmol) in dioxane, 4-ethyl-2-iodoanisole (0.595 g, 2.27 mmol) from Step A was added. The reaction was stirred at 80 C for 4 h then cooled to room temperature. After filtration to remove insoluble material, the solution was diluted in ethyl acetate, washed with water then brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by flash chromatography using 10% EtOAc/hexane. ¹H NMR (CDCl3,600 MHz) 8 7.50 (d, J = 2.4 Hz, 1H), 7.22 (dd, J = 8.4,2.4 Hz, 1H), 6.80 (d, J = 8.4 Hz, 1H),3.82 (s, 3H), 2.59 (q, J = 15.6,7.8 Hz, 2H), 1.36 (s, 12H), 1.22 (t, J = 7.8 Hz, 3H). LC-MS (M+1) 263.3 (3.90 min). Step C: Methyl f3,5-bis(trifluoromethyl)benzyIl f5'-ethyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2- yl] methyl}carbamate A mixture of methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate (105 mg, 0.18 mmol) (Example 5), the title compound from Step B (58 mg, 0.22 mmol), anhydrous potassium carbonate (50 mg, 0.36 mmol), dichloro[1,1'-bis(diphenylphospino) ferrocene]palladium(H) dichloromethane adduct (14.7 mg, 0.018 mmol), and a catalytic amount of palladium acetate in anhydrous dioxane were stirred at 80 C for approximately 40 hours. The solvent was removed in vacuo, and the title compound was obtained by preparative thin layer chromatography using 60% CH2Cl2/hexane. ¹H NMR (CDCl3,600 MHz) No. 7.71 (s, 1H), 7.56 (d, J = 7.8 Hz, 1H), 7.45 (m, 2H), 7.32 (d, J = 7.8 Hz, 1H), 7.25 (m, 1H), 7.21 (m, 1H), 6.88 (d, J = 2.4 Hz, 1H), 6.87 (m, 1H), 4.23-4.56 (m, 4H), 3.74 (m, 3H), 3.68 (s, 3H), 2.60 (m, 2H), 1.24 (m, 3H). LC-MS (M+1) 594.0 (4.76 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 73 Ethyl-4-keto-gamma-(5-ethyl-2-methoxyphenyl)butyrate Using the procedure as described for Example 53 but starting with <strong>[1515-95-3]p-ethylanisole</strong>, afforded the desired compound, M+ 264. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7 2-Aminomethyl-4-ethyl-6-sulfamoylphenol hydrochloride The compound is prepared analogously to the sequence of reactions described in Example 1, but using 4-ethylanisole as the starting material. The intermediate products and the end product have the following melting points: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium chloride; In dichloromethane; chloroform; | EXAMPLE 15 5-Ethyl-2-hydroxy-4'-trifluoromethyl benzophenone Aluminium chloride (0.6 g, 0.004 mole) was stirred in dichloromethane (2 ml) and treated with 4-trifluoromethylbenzoyl chloride (1 g, 0.0048 mole) (ice-bath cooling) and then with 4-ethylanisole (0.6 g, 0.0044 mole) in dichloromethane (1 ml). The mixture was stirred at room temperature overnight and then poured into ice and concentrated hydrochloric acid and extracted with chloroform. The chloroform solution was washed with 10% NaHCO3 solution (100 ml), dried (MgSO4), filtered and evaporated to leave 5-ethyl-2-methoxy-4'-trifluoromethylbenzophenone (1.2 g) as a yellow oil. The latter was heated in 55% aqueous hydrogen bromide (27.5 ml) at 110-120 C. for 5 hours. The mixture was evaporated to dryness to leave the required product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium chloride; In dichloromethane; | EXAMPLE 16 5-Ethyl-2-hydroxy-3'-carboxy- and 3'-carbomethoxybenzophenone Aluminium chloride (39.9 g, 0.3 mole) was stirred in dichloromethane (133 ml) and treated with 3-carbomethoxybenzoyl chloride (59.5 g, 0.3 mole) (ice-bath cooling), over 0.5 hours.4-Ethylanisole (40.8 g, 0.3 mole) in dichloromethane (70 ml) was added to the stirred, cooled mixture, which was then stirred at room temperature overnight. The reaction mixture was processed as in Example 15 to leave 5-ethyl-2-methoxy-3'-carbomethoxybenzophenone. The latter was heated in 55% aqueous hydrogen bromide (500 ml) at 110-120 C. for 5 hours. The mixture was evaporated to dryness to leave 5-ethyl-2-hydroxy-3'-carboxybenzophenone, which was characterised by having the correct C, H and N microanalysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90%Spectr. | With triethylsilane; In dichloromethane; at 20℃; for 0.666667h; | General procedure: In around-bottomed flask was placed 30 mg of Sn-Mont, 1 mmol of 1a, 2 mmol of Et3SiH and 5 mL of CH2Cl2. The mixturewas stirred at room temperature for 40 min. Then, Sn-Mont was filtered off, andthe filtrate was concentrated and analyzed by NMR using mesitylene as theinternal standard. In order to completely stop the reactions in entries 1 to 5 of Table 2, the reaction mixtures were cooled down in an ice-waterbath for 10 min just after the specified reaction times, and then the clay wasfiltered off. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | n-Butyl lithium (2.5M in hexanes, 38.5 ml, 100.0 mmol) was added dropwise under a nitrogen atomosphere to a stirred solution of 4-ethylanisole (11.7 g, 86.0 mmol) and N1N1N', N'- tetramethylethylenediamine (10 ml, 88.0 mmol) in anhydrous diethyl ether (100 ml) and the mixture was stirred and held at 300C for 16 hours. The mixture was cooled and poured slowly in to a mixture of excess solid carbon dioxide in anhydrous diethyl ether. Upon warming to room temperature the mixture was made basic by the addition of 2M sodium hydroxide, the aqueous layer was separated and acidified to pH 2 or below by the addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether, the organic layer separated and the solvent removed in vacuo to afford 5-ethyl-2-methoxybenzoic acid (5.7 g, 37%) as a pale yellow oil. 1H NMR (DMSO- dbeta) 12.50 (1 H, br s), 7.48 (1 H, d), 7.33 (1 H, dd), 7.03 (1 H, d), 2.56 (2H, q), 1.17 (3H, q). MS: [M+H]+ 181. | |
37% | n-Butyl lithium (2.5M in hexanes, 38.5 ml, 100.0 mmol) was added dropwise under a nitrogen atomosphere to a stirred solution of 4-ethylanisole (11.7 g, 86.0 mmol) and N,N,N',N'- tetramethylethylenediamine (10 ml, 88.0 mmol) in anhydrous diethyl ether (100 ml) and the mixture was stirred and held at 300C for 16 hours. The mixture was cooled and poured slowly in to a mixture of excess solid carbon dioxide in anhydrous diethyl ether. Upon warming to room temperature the mixture was made basic by the addition of 2M sodium hydroxide, the aqueous layer was separated and acidified to pH 2 or below by the addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether, the organic layer separated and the solvent removed in vacuo to afford 5-ethyl-2-methoxybenzoic acid (5.7 g, 37%) as a pale yellow oil. 1H NMR (DMSO- d6) 12.50 (1H, br s), 7.48 (1 H, d), 7.33 (1 H, dd), 7.03 (1 H, d), 2.56 (2H, q), 1.17 (3H, q). MS: [M+H]+ 181. | |
37% | n-Butyl lithium (2.5M in hexanes, 38.5 ml, 100.0 mmol) was added dropwise under a nitrogen atomosphere to a stirred solution of 4-ethylanisole (11.7 g, 86.0 mmol) and lambda/.lambda/.lambda/'.lambda/1- tetramethylethylenediamine (10 ml, 88.0 mmol) in anhydrous diethyl ether (100 ml) and the mixture was stirred and held at 3O0C for 16 hours. The mixture was cooled and poured slowly in to a mixture of excess solid carbon dioxide in anhydrous diethyl ether. Upon warming to room temperature the mixture was made basic by the addition of 2M sodium hydroxide, the aqueous layer was separated and acidified to pH 2 or below by the addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether, the organic layer separated and the solvent removed in vacuo to afford 5-ethyl-2-methoxybenzoic acid (5.7 g, 37%) as a pale yellow oil. 1H NMR (DMSO- d6) 12.50 (1H, br s), 7.48 (1 H, d), 7.33 (1H, dd), 7.03 (1 H, d), 2.56 (2H, q), 1.17 (3H, q). MS: [M+H]+ 181. |
37% | n-Butyl lithium (2.5M in hexanes, 38.5 ml, 100.0 mmol) was added dropwise under a nitrogen atmosphere to a stirred solution of 4-ethylanisole (11.7 g, 86.0 mmol) and N,N,N',N'-tetramethylethylenediamine (10 ml, 88.0 mmol) in anhydrous diethyl ether (100 ml) and the mixture was stirred and held at 30 C. for 16 hours. The mixture was cooled and poured slowly in to a mixture of excess solid carbon dioxide in anhydrous diethyl ether. Upon warming to room temperature the mixture was made basic by the addition of 2M sodium hydroxide, the aqueous layer was separated and acidified to pH 2 or below by the addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether, the organic layer separated and the solvent removed in vacuo to afford 5-ethyl-2-methoxybenzoic acid (5.7 g, 37%) as a pale yellow oil. 1H NMR (DMSO-d6) 12.50 (1H, br s), 7.48 (1H, d), 7.33 (1H, dd), 7.03 (1H, d), 2.56 (2H, q), 1.17 (3H, q). MS: [M+H]+ 181. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | n-Butyl lithium (2.5M in hexanes, 38.5 ml, 100.0 mmol) was added dropwise under a nitrogen atomosphere to a stirred solution of 4-ethylanisoie (11.7 g, 86.0 mmol) and N, N, N', N'- tetramethylethylenediamine (10 ml, 88.0 mmol) in anhydrous diethyl ether (100 ml) and the mixture 5 was stirred and held at 3O0C for 16 hours. The mixture was cooled and poured slowly in to a mixture of excess solid carbon dioxide in anhydrous diethyl ether. Upon warming to room temperature the mixture was made basic by the addition of 2M sodium hydroxide, the aqueous layer was separated and acidified to pH 2 or below by the addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether, the organic layer separated and the solvent removed in 0 vacuo to afford 5-ethyl-2-methoxybenzoic acid (5.7 g, 37%) as a pale yellow oil. 1H NMR (DMSO- d6) 12.50 (1 H, br s), 7.48 (1 H, d), 7.33 (1 H, dd), 7.03 (1 H, d), 2.56 (2H, q), 1.17 (3H, q). MS: [M+H]+ 181. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
STEP B 5-Ethyl-2-hydroxy-phenyl-methanone; Aluminum chloride (0.58 g, 4.4 mmol) is added in portions top- ETHYLANISOLE (0.50 g, 3.7 mmol) in DCM (3.4 mL) at 0 C under N2, and the mixture is stirred for about 10 minutes, and then benzoyl chloride (0.43 mL, 3.9 mmol) is added dropwise. The mixture is stirred at 0 C for 4 h and poured in ice. The mixture is warmed to ambient temperature and extracted with EtOAc. Organic layers are combined and washed with aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to obtain yellow oil. Crude mixture is dissolved in toluene (4.3 ML) and aluminum chloride (0.49 g, 3.7 mmol) is added in portions at ambient temperature, and stirred under N2. The mixture is warmed at 80 C for 3 h and additional 16 h at 55 C. The mixture is cooled to ambient temperature and poured in ice. The mixture is extracted with EtOAc. Organic phases are combined and washed with aqueous sodium chloride, and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography, silica, eluting with hexanes: EtOAc (98: 2) provides the title compound as a yellow oil that crystallizes with the time: ES+ (m/e) 227.10 (M+H) +, RF 0. 65 hexanes: EtOAc (90: 10).; A 0 C solution of 4-etliylanisole (10.0 g, 73.4 mmol) in dry CH2Cl2 (100 mL) is treated portion wise with aluminum chloride (11.7 g, 87.7 mmol). The 0 C reaction mixture is then treated dropwise with benzoyl chloride (11. 38 g, 81. 0 mmol) and the reaction is stirred at 0 C for 1 hour under N2. The reaction is poured into ice water and extracted with CH2C12. The organic layer is dried (NA2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/EtOAc to afford 14.72 g (83%) of the title compound. Rf= 0.34 (4/1 HEXANES/ETOAC). 1H NMR (400 MHz, CDC13) ; MS (ES+) NZLZ mass calcd for CL6HL6O2 240, found 241 (M + 1, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 13 2- {4- [3- (2-CYCLOHEXANECARBONYL-4-ETHYL-PHENOXY)-BUTOXY]-PHENOXY-2-METHYL-PROPIONIC acid Step A CYCLOHEXYL- (5-ETHYL-2-HYDROXY-PHENYL)-METHANONE; Aluminum chloride (0. 35 g, 2.6 mmol) is added in portions top- ethylanisole (0.30 g, 2.2 mmol) in DCM (2.2 mL) at 0 C under N2. After stirring the mixture FORLO min. , cyclohexanecarbonyl chloride (0.32 mL, 2.4 mmol) is added dropwise. The mixture is stirred at 0 C for 4 h and poured in ice. The mixture is warmed to ambient temperature and extracted with EtOAc. Organic layers are combined, washed with aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to obtain a yellow oil. The crude mixture is dissolved in toluene (2.6 mL) and aluminum chloride (0.29 g, 2.2 mmol) is added in portions at ambient temperature. The mixture is stirred under N2, and warmed at 80 C for 3 h and for 16 h at 55 C. The mixture is cooled to ambient temperature and poured in ice. It is extracted with EtOAc, and organic phase is combined, washed with aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash silica gel chromatography, eluting with hexanes: EtOAc (97: 3) provides the title compound as a yellow oil: ES+ (m/e) 233.15 (M+H) +, RR 0. 68 hexanes: EtOAc (90: 10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 11 2-F4- [3-ETHYL-2-ISOBUTYRYL-PHENOXY)-BUTOXY]-PHENOXY}-2-METHYL-PROPIONIC ACID STEP A 1- (5-ETHYL-2-HYDROXY-PHENYL)-2-METHYL-PROPAN-1-ONE; Aluminum chloride (0.35 g, 2.6 mmol) is added in portions top- ethylanisole (0.30 g, 2.2 mmol) in DCM (2.2 mL) at 0 C under N2. After stirring the mixture for 10 min. , isobutyryl chloride (0.25 mL, 2.4 mmol) is added dropwise. The mixture is stirred at 0 C for 4 h and then poured in ice. The mixture is warmed to ambient temperature and then extracted with EtOAc. Organic layers are combined, washed with aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain a yellow oil. The crude mixture is dissolved in toluene (2.6 mL), and aluminum chloride (0.29 g, 2.2 mmol) is added in portions at ambient temperature, and then stirred under N2. The mixture is warmed at 80C for 3 h and for 16 h at 55 C. The mixture is cooled to ambient temperature and poured in ice. The mixture is extracted with EtOAc. Organic phase is combined and washed with aqueous sodium chloride, and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash silica gel chromatography, eluting with hexanes : EtOAc (97: 3) provides the title compound as a yellow oil (0.35 g, 1.82 mmol, 83%): ES+ (m/e) 193.16 (M+H) +, RF = 0.37 hexanes: EtOAc (90: 10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | STEP B (5-Ethyl-2-methoxy-phenyl)-pyridin-2-yl-methanone; A-10 C solution of N, N, N', N -TETRAMETHYLETHYLENEDIAMINE (1.31 g, 11.3 mmol) is treated dropwise with a 1.6 M solution of n-butyllithium in hexanes (7.2 mL, 11. 5 mmol), and the reaction is stirred at-10 C under N2. 4-Ethylanisole (1. 08 g, 7.93 mmol) is then added dropwise, and the mixture is stirred at-10 C under N2, Pyridine-2- carboxylic acid methoxy-methyl-amide (1.47 g, 8.85 mmol) is added and the mixture is stirred at-10 C for 40 minutes under N2. The mixture is quenched with water and extracted with ET20. The organic layer is dried (NA2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by column chromatography using 7/1 hexanes/acetone to afford 0.132 g (6%) of the title compound. Rf= 0.38 (1/1 HEXANES/ETOAC). 1H NMR (400 MHz, CDC13) ; MS (ES+) 7N/Z mass calcd for CL5HI502N 241, found 242 (M+1, 100%). |
Tags: 1515-95-3 synthesis path| 1515-95-3 SDS| 1515-95-3 COA| 1515-95-3 purity| 1515-95-3 application| 1515-95-3 NMR| 1515-95-3 COA| 1515-95-3 structure
[ 5406-18-8 ]
3-(4-Methoxyphenyl)propan-1-ol
Similarity: 0.94
[ 5406-18-8 ]
3-(4-Methoxyphenyl)propan-1-ol
Similarity: 0.94
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P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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