| 70% |
With sodium ethanolate; In toluene; at 0 - 100℃; for 3h; |
To a mixture of sodium ethoxide (1.95 g, 28.6 mmol) in toluene(50 mL) was added diester (4.0 g, 14.3 mmol) dropwise at 0 C. Thereaction was stirred at 100 C for 3 h. Then the reaction was quenchedwith H2O (9 mL) and acetic acid (1.6 mL, 28.0 mmol). The mixture wasstirred at room temperature for 1 h and extracted with EtOAc (50 mL).The organic layer was washed with brine (20 mL), dried over MgSO4,filtered and evaporated to give the product (2.5 g, 70% yield) withoutfurther purification. 1H NMR (600 MHz, CDCl3) delta (ppm): 7.38-7.35 (m,5H), 3.75 (s, 3H), 3.67 (m, 3H), 3.21 (t, J=1.5 Hz, 2H), 2.65 (t,J=5.9 Hz, 2H), 2.43 (ddd, J=5.9, 4.3, 1.6 Hz, 2H). MS-ESI:[M+H]+: 248.5. |
|
With sodium methylate; In toluene; at 90℃; for 3h; |
27.0 g of 27% sodium methoxide, 33.4 g (0.12 mol) of crude diester and 300 ml of toluene were charged into a 500-ml three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a fractionating apparatus, and the reaction was carried out with stirring at an internal temperature of 90C or higher , 50 ml of toluene was added, and the reaction was further continued for 3 hours.Cooled to room temperature, neutralized to pH 6 with acetic acid, and the layers were allowed to stand.Separate the toluene layer, with 22% hydrochloric acid 150ml 3 times extraction.The hydrochloric acid extracts were combined and the reaction was heated with stirring for 4 hours.Decompression distillation recovery of hydrochloric acid (about 120 ml of distilled hydrochloric acid), distilled liquid cooled to below 10 , with 40% sodium hydroxide PH12 above.The mixture was extracted three times with 80 ml of ethyl acetate. The ethyl acetate extracts were combined, and the residue was dried over anhydrous sodium sulfate.Ethyl acetate was removed by distillation at atmospheric pressure and dried in vacuo to give 19 g of the crude product of the hydrolyzate (E) in a yield of 84% |
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With sodium methylate; In toluene; at 0 - 85℃; for 3.5h; |
To a solution of sodium methoxide (0.58 g, 10.75 mmol) in toluene(30 mL) was added compound 23 (2 g, 7.17 mmol) dropwise at 0 C.The reaction was stirred at 85 C for 3.5 h. Then the reaction wasquenched with H2O (5 mL) and acetic acid (0.6 mL, 10.75 mmol). Andthe mixture was stirred at r.t. for 1 h. The reaction was extracted withethyl acetate, dried over MgSO4, evaporated to receive the product(1.2 g, 67% yield) without purification. 1H NMR (600 MHz, CDCl3) delta(ppm): 7.38-7.35 (m, 5H), 3.75 (s, 3H), 3.67 (m, 3H), 3.21 (t,J=1.5 Hz, 2H), 2.65 (t, J=5.9 Hz, 2H), 2.43 (ddd, J=5.9, 4.3,1.6 Hz, 2H). MS-ESI: [M+H]+: 248.5. |
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