| 74% |
With titanium tetrachloride; zinc; In tetrahydrofuran; for 15h;Reflux; |
4,4'-dimethoxybenzophenone 1 (5.00 g, 20.6 mmol) and zinc powder(6.66 g, 10.7 mmol) was dissolved in 100 ml of THF, And TiCl4 (7.50 mL, 68.4 mmol) was slowly added dropwise thereto, followed by heating and refluxing for 15 hours.After cooling the reaction solution to room temperature, 100 ml of water was added, and the solution was extracted three times with 100 ml of chloroform, and each of the extracts was combined, dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure, The residue was recrystallized from a chloroform: hexane = 2: 1 solvent to give 3.43 grams of compound 2 as white crystals in a yield of 74%. |
| 70% |
With titanium tetrachloride; zinc; In tetrahydrofuran;Reflux; |
TiCl4( 1.5 mL, 2.14mmol) was added dropwise to solution of bis(4-methoxyphenyl)methanone ( 1g, 4.12 mmol) and Zinc powder ( 1.33 g, 2.14mmol) in THF (20 mL) at room temperature. The mixture was refluxed until all the starting material was consumed. After cooling to room temperature, reaction mixture was hydrolyzed by the addition of H2O (20 mL). After concentrating in the vacuo, mixture was extracted with DCM. Combined organic phases are dried over anhydrous Na2SO4 and concentrated in vacuo. Obtained crude mixture was subjected to silica gel FCC using EtOAc/Hexane (1/5, v/v) as the eluent giving the compound 3 (0.65 g, 70%).1HNMR (400 MHz, CDCl3): d 6.97(d, J = 8.60 Hz, 8H), 6.67 (d, J = 8.71 Hz, 8H), 3.77 (s, 12H). 13CNMR (100 MHz, CDCl3): d 157.8, 152.5, 138.3, 136.9, 132.5,113.0, 55.0 ppm. MS(TOF- ESI): m/z: Calcd for C30H28O4: 453.20604[M+H]+ , Found: 453.20870 [M+H]+ , Δ=-5.88 ppm. |
| 70% |
With titanium tetrachloride; zinc; In tetrahydrofuran; at 80℃; for 12h;Reflux; |
A typical procedure for synthesis of Compound 2 was as follows. Zn dust (1.84g, 28mmol) and TiCl4 (1.58mL, 14mmol) were refluxed for 2h in 50mL of dry THF under N2 atmosphere. A solution of 4,4-dimethoxybenzophenone (1.50g, 7.0mmol) in dry THF (20mL) was added to the preceding suspension, and then the reaction was refluxed at 80C for 12h. An aqueous solution containing 10% K2CO3 (50mL) was added after the reaction mixture was cooled down to room temperature. The resulting product was extracted with ethyl acetate. The solvent was evaporated under vacuum and the crude product was purified by a silica gel column using hexane-ethyl: acetate (1:1, v/v) as the eluent. Compound 2 was obtained in 70% yield (1.01g). 1H NMR (600MHz, CDCl3) δ (ppm) 6.93 (d, J=6Hz, 8H), 6.64 (d, J=6Hz, 8H), 3.77 (s, 12H). 13C NMR (150MHz, CDCl3) δ(ppm) 158.96, 138.08, 138.07, 133.75, 114.19, 56.28. HRMS (ESI) m/z: [M+K+] 491.1633, (calcd. for C30H28O4, 452.0653). |
| 49.3% |
With titanium tetrachloride; zinc; In tetrahydrofuran; for 20h;Inert atmosphere; |
4 g of 4,4 '-dimethoxybenzophenone and 6.7 g of zinc powder were added to a 250 mL three-necked flask. Under N2 protection, 100 mL of ultra dry solvent THF was added and stirred well. 13.7 g of TiCl4 was added dropwise with a constant pressure dropping solution. After the completion of the dropwise addition, stirring was continued (20 h), and the reaction was stopped and cooled to room temperature. Quenched by adding 10% sodium carbonate solution until no gas is released, and filtered water added (100 ml x 3) and extracted with CHCl 3, the organic phase was dried over anhydrous magnesium sulfate, and rotary evaporated to give a white solid. (100 ml x 3) and extracted with CHCl 3, the organic phase was dried over anhydrous magnesium sulfate, and rotary evaporated to give a white solid compound A 2.30g, yield 49.3%. |
| 42% |
With titanium tetrachloride; zinc; In tetrahydrofuran; at 66℃; for 16h;Inert atmosphere; Cooling with ice; |
Zinc powder (2.7 g) was added to 4,4-dimethoxybenzophenone (2.0 g) in anhydrous tetrahydrofuran (40 ml), and cooled in an ice water bath under nitrogen atmosphere. The syringe was slowly added with titanium tetrachloride (3.5 ml, stirring constantly, transferred to an oil bath at 66 C, and heated to reflux for 16 hours; quenched by adding 10% potassium carbonate solution (mass fraction) to obtain black green Oily liquid; purified by silica gel column chromatography to give TPE-OMe (0.97 g; 42%) |
|
With titanium tetrachloride; zinc; In tetrahydrofuran; at -78 - 80℃; for 24h;Inert atmosphere; |
Using dimethoxybenzophenone as raw material,TPE-4OMe is prepared through one-step McMurry coupling reaction;The specific synthesis scheme is as follows:Dimethoxybenzophenone (8.0mmol)And zinc powder (2.08g, 32mmol) was placed in a dry two-necked flask with magnetic stirring.Then freshly distilled tetrahydrofuran (50ml) was placed under N2 atmosphere, then the reactor was transferred to a cryostat and stirred for 10 minutes (-78).Finally, titanium tetrachloride (1.73ml, 16mml) was injected into the reactor through a syringe and stirred for 30 minutes.After that, the reaction returned from low temperature to room temperature, and then heated to 80C for 24 hours.Then cool to room temperature.Quench the reaction with water and add K2CO3 (10%) solution,It was extracted 3 times with DCM.The collected organic layer was dried over anhydrous Na2SO4 and spin-dried under vacuum to obtain the desired crude product.Purify by column chromatography to obtain the target compound TPE-4OMe. |
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