Application of 124937-73-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol. A new synthetic method of this compound is introduced below.
Example 1; Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate (Vb); This intermediate is of significant importance for use in the preparation of Tolterodine or salts thereof, or its derivatives according to the present invention.In a 3-necked round bottom flask, 6-methyl-4-phenyl-3,4-dihydro coumarin (II, 100 g, 0.420 mol) is charged into methanol (500 ml) at about 25 C. with stirring. To the resulting suspension, potassium carbonate (K2CO3, 87 g, 0.63 mol) and methyl iodide (MeI, 78 ml, 1.25 mol) are added and the mass is stirred at from about 55 C. to about 60 C. for 4 h. The reaction mass is cooled to from about 40 C. to about 45 C. and MeI (27 ml, 0.43 mol) and K2CO3 (29 g, 0.21 mol) are added. Re-heat the mass to 5560 C. and stir for additional 6 h until the reaction completes. Then solvent is removed by distillation under vacuum. The residue is dissolved in 350 ml of toluene. This organic phase is washed once with 750 ml of DM water and twice with 450 ml of DM water.The organic layer thus obtained is charged into a 3-necked round bottom flask under N2 atmosphere and cooled at temperature from about -5 C. to about 5 C. Toluene solution of sodium bis(2-methoxyethoxy) aluminum hydride (Red-Al, 200 ml, 70% w/v, 0.706 mol) is slowly added through a dropping funnel over a period of 120 min, maintaining the solution temperature within -55 C. The mixture is stirred for an additional 1 h at this temperature until the reaction completes. Then aqueous solution of NaOH (80 ml, 10%) is added through a dropping funnel over a period of 45 min, maintaining the temperature at 010 C., and continue stirring for an additional 45 min at the same temperature. Add 750 ml of DM water and stir for 30 min at 25 C. The biphasic reaction mass is filtered through a celite bed (10 g). The organic layer is collected and dried over 20 g of anhydrous sodium sulfate (Na2SO4). The solids are filtered and washed with 50 ml of toluene. The toluene is distilled off completely and compound IV is obtained as slightly yellow thick oil.The thick oil is dissolved in 300 ml of dichloromethane (DCM) under N2 atmosphere. Triethylamine (Et3N, 90 ml, 0.647 mol) is added and the mass is cooled to 05 C. Mesyl chloride (MsCl, 36 ml, 0.465 mol) is added slowly through a dropping funnel over a period of 120 min, keeping the solution temperature below 10 C. Continue stirring the mixture for an additional 1 h at 05 C. until the reaction completes. 1 L of cold DM water (05 C.) was added and the mass is stirred for 3060 min at this temperature. Conc. HCl (25 ml) is added and the mass is stirred until it reaches 25 C. The organic layer is collected and washed with 200 ml of DM water. About 180220 ml of DCM is distilled off from the organic layer under atmosphere pressure at 3843 C. 400 ml of cyclohexane is added to the residue and the mass is heated to reflux till a clear solution is obtained (7080 C.). This solution is cooled slowly and compound Vb crystallized. The solid is filtered in Buchner funnel and spray washed with 100 ml of cold cyclohexane. The mass is dried under vacuum at 60 C. to give 90110 g of title compound.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,124937-73-1, 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, and friends who are interested can also refer to it.
Reference:
Patent; PHARMATHEN S.A.; US2012/41235; (2012); A1;,
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