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With manganese(IV) oxide In dichloromethane at 20℃; for 24 h;
According to a modified procedure from Azuma et al (Tetrahedron, 2013, 69(6), 1694-1699), MnO2 (8.4 g, 96.7 mmol, 10 eq) was added to a stirring solution of di(naphthalen-2-yl)methanol (2.75 g, 9.68 mmol, 1.0 eq) in DCM (20 mL) at room temperature. The solution was stirred for 24 hours. The reaction mixture was then filtered over Celite® and concentrated in vacuo to give the desired di(naphthalen-2-yl)methanone (2.70 g, 9.56 mmol, 99percent) as colourless solid. The molecule was used without further purification. 1H NMR (400 MHz, CDCl3) δH/ppm 8.34 (s, 2 H), 8.00-8.03 (m, 4 H), 7.95 (apparent t, J=7.2 Hz, 4 H), 7.65 (apparent td, J=7.6, 1.2 Hz, 2 H), 7.58 (apparent td, J=7.6, 1.2 Hz, 2 H). 13C NMR (100 MHz, CDCl3) δC/ppm 196.8 (1 C), 135.3 (2 C), 135.2 (2 C), 132.3 (2 C), 131.8 (2 C), 127.8 (4 C), 126.8 (4 C), 125.9 (4 C). MS (ESI) [M+Na]+: 305.1 (100). IR (vmax/cm−1): 2915, 1653, 1379, 1334, 1194, 763
With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; silver nitrate In acetone at 40℃; for 24 h; Autoclave; Inert atmosphere
General procedure: The reaction was carried out in an autoclave containing a 10mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP(0.04 mmol), and a magnetic stir bar were placed in the tubewhich was then capped with a stopper and flushed withargon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),and acetone (3 mL) were added to the tube. The tube was putinto the autoclave. Once sealed, the autoclave was purgedseveral times with CO, pressurized to 1 atm at r.t. and thenheated in an oil bath at 40 °C for 24 h. The autoclave wasthen cooled to r.t. and carefully vented to discharge CO in afume hood. Water (10 mL) was added, and the product wasextracted with CH2Cl2 (3 × 15 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated. Thecrude product was purified by column chromatography onsilica gel using a mixture of EtOAc and PE as eluent to givethe products. The identity and purity of the product wasconfirmed by 1H NMR and 13C NMR spectroscopy and MSor HRMS spectrometry.
With copper(l) iodide; 5% Pd-CaCO3; In dimethyl sulfoxide; at 50℃; under 114.008 - 1406.09 Torr; for 12h;
General procedure: Phenylboronic acid (0.249 g, 2 mmol),5wt% Pd/CaCO3 (0.0456g, Pd 0.01mmol)And CuI (0.0114g, 0.03mmol)Add to a 250 mL polytetrafluoro-lined pressure reactor,Add DMSO (10 mL),Install the reactor,Slowly pass 1.85atm of air into the fume hood.Then pass 0.15atm CO,The reaction kettle was then placed in a 50 C oil bath for 12 hours.After the reaction was stopped, the reaction vessel was cooled to room temperature, and the remaining gas in the kettle was slowly discharged in a fume hood.Turn on the reaction kettle and add 40 mL of ammonia water with a concentration of 5%.The palladium catalyst is separated by filtration, and the catalyst can be reused after washing and drying.The mother liquor was extracted three times with dichloromethane (30 mL). EtOAc was evaporated.Purified by column chromatography (20:1 by volume of petroleum ether / ethyl acetate as eluent)Obtaining 0.173 g of benzophenone in a yield of 95%, the product is a white solid.
NAPHTHALEN-2-YL KETONE STR21 Into a 1 liter reaction vessel equipped with stirrer, thermometer, reflux condenser and heating mantle is placed 260 grams of a 50:50 mixture of the compounds having the structures: STR22 and 25 grams of sodium carbonate. The reaction mass is heated to 45-50 C. and maintained at 45-50 C. with stirring. Over a period of one hour, 230 grams of peracetic acid is added to the reaction mass while maintaining the temperature at 45-50 C. The reaction mass is then washed with one volume of water, followed by one volume of 50% sodium hydroxide (aqueous). The reaction mass is then distilled on a fractionation column yielding the following fractions: Fractions 2-5 are bulked. Bulked distillation Fractions 2-5 have a patchouli, musky, sweet, woody, animalic and civet aroma, with woody and patchouli topnotes. FIG. 1 is the GLC profile for the reaction product. FIG. 2 is the NMR spectrum for the reaction product which has the two compounds having the structures: STR23
With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; silver nitrate; In acetone; at 40℃; under 760.051 Torr; for 24h;Autoclave; Inert atmosphere;
General procedure: The reaction was carried out in an autoclave containing a 10mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP(0.04 mmol), and a magnetic stir bar were placed in the tubewhich was then capped with a stopper and flushed withargon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),and acetone (3 mL) were added to the tube. The tube was putinto the autoclave. Once sealed, the autoclave was purgedseveral times with CO, pressurized to 1 atm at r.t. and thenheated in an oil bath at 40 C for 24 h. The autoclave wasthen cooled to r.t. and carefully vented to discharge CO in afume hood. Water (10 mL) was added, and the product wasextracted with CH2Cl2 (3 × 15 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated. Thecrude product was purified by column chromatography onsilica gel using a mixture of EtOAc and PE as eluent to givethe products. The identity and purity of the product wasconfirmed by 1H NMR and 13C NMR spectroscopy and MSor HRMS spectrometry.
N-(2-chloropyridin-3-yl)-N’-(di-naphthalen-2-ylmethylene)hydrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76.1%
With toluene-4-sulfonic acid; In ethanol; toluene; for 6h;Reflux;
A mixture of (2-chloro-pyridin-3-yl)-hydrazine monohydrate(4.0 g, 24.8 mmol)prepared in Step 1 of Preparation 3, ethanol(16.0 mL), toluene(16.0 mL), 2,2?-dinaphthylketone (8.4 g, 29.8 mmol), andp-toluenesulfonic acid monohydrate (0.5 g, 2.5 mmol) was refluxed for 6 hours. The reaction mixture was cooled to room temperature, stirred for 2 hours, and then filtered under reduced pressure. The resulting solid was dried to give 7.7 g of the titled compound. (Yield: 76.1%)1H-NMR(400MHz, CDC13) oe 8.22(d, 1H), 8.20(s, 1H), 8.13(d, 1H), 8.08(d, 1H), 8.O1(d, 1H), 7.94(d, 2H), 7.87(d, 2H), 7.84(d, 1H), 7.57-7.67(m, 4H), 7.40-7.50(m,2H), 7.24-7.27(m, 1H)
N-(di(naphthalen-2-yl)methyl)propan-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
TiCl4 (10.3 mL, 10.3 mmol, 1.1 eq, 1 M solution in DCM) was added slowly to an ice-bathed solution of <strong>[613-56-9]di(naphthalen-2-yl)methanone</strong> (2.65 g, 9.38 mmol, 1.0 eq) in DCM (50 mL). The solution was stirred for 10 minutes at room temperature and then a solution of isopropylamine (1.8 mL, 20.6 mmol, 2.2 eq) in THF (10 ml, 2 M solution) was added dropwise to the reaction mixture. The reaction flask was stirred for 3 hours. A solution of NaB(CN)H3 (0.71 g, 11.2 mmol, 1.2 eq) in THF (12 mL, 1 M solution) was added slowly to the reaction mixture. MeOH (17 mL) was added slowly to the reaction mixture. The reaction mixture was stirred at room temperature for 18 hours. NaOH (25 mL, 2M aq solution) was added slowly and the reaction mixture was stirred for 30 min. The reaction mixture was filtered on Celite and washed with EtOAc (20 mL). NaHCO3 (aq. sat., ca 15 mL) were added to the suspension. The mixture was partitioned between the aqueous and organic layers and the aqueous phase extracted with EtOAc (3×20 mL). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuo to give an oil. Purification by flash column chromatography (93:7; Petrol/EtOAc; SiO2) gave N-(di(naphthalen-2-yl)methyl)propan-2-amine (2.24 g, 6.9 mmol, 74%) as a colourless solid. 1H NMR (400 MHz, CDCl3) deltaH/ppm 8.15 (s, 2 H), 8.03 (d, J=8.1 Hz, 2 H), 7.95 (d, J=8.4 Hz, 4 H), 7.74 (dd, J=8.4, 1.5 Hz, 2 H), 7.56-7.67 (m, 4 H), 5.51 (s, 1 H), 3.06 (spt, J=6.2 Hz, 1 H), 1.72 (br. s., 1 H), 1.36 (d, J=6.2 Hz, 6 H). 13C NMR (100 MHz, CDCl3) deltaC/ppm 141.8 (2 C), 133.4 (2 C), 132.6 (2 C), 128.2 (2 C), 127.9 (2 C), 127.6 (2 C), 126.0 (2 C), 125.9 (2 C), 125.7 (2 C), 125.6 (2 C), 64.3 (1 C), 46.2 (1 C), 23.3 (2 C). HRMS (ESI) m/z calcd for C32H52N [M+H]+: 326.1888, found: 326.1903. IR (vmax/cm-1): 3055, 2960, 1600, 1362, 907, 757, 734
[Reaction Formula 40]The experimental apparatus was sufficiently dried and 17.0 g (11.8 mm1, 1.1 eq.) Was added to a 2 L three-necked flask,Of the intermediate-36, 360 ml of dry tetrahydrofuran was added, dissolved and cooled to -78 C, 5.1 ml of 2.5 M (12.8 mmol, 1.2 eq.) Of n-BuLi was added dropwise.After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour, and then 3.0 g (10.7 mmol, 1.0 eq.) Was added dropwise at that temperature,2- (2-naphthyl) methanone, and the mixture was stirred at room temperature for 12 hours.After completion of the reaction, 4M hydrochloric acid solution was added and extracted with methylene chloride. The organic phase was washed with saturated brine to neutral, dried, the solvent was removed, dried sufficiently, and then charged to a 2 L dry three-necked flask, heated to 120 C, 5 hours, the end of the reaction.Cooled to room temperature, the solvent was removed,The reaction mixture was dried over toluene and ethanol to give 10.7 g of compound 77 in a yield of61%.
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