3 - (4 - 氟苯基)丙烯酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4 g. of sodium hydroxide in 30 ml. of water is added to a solution of 19.4 g. (0.1 mole) of ethyl trans-4-fluorocinnamate (Compound LXV) in 350 ml. of ethanol, and the reaction mixture is stirred at 70° C. for 18 hours. The solvent is evaporated at reduced pressure, and the residue is dissolved in water. The solution is washed once with methyl t-butyl ether and acidified with 6N. hydrochloric acid. The resulting precipitate is washed twice with water and dried to obtain the product (15.5 g. (93%)). An analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C. The solvent is evaporated at reduced pressure the residue is dissolved in water The solution is washed once with methyl t-butyl ether The resulting precipitate is washed twice with water dried to obtain the product (15.5 g. (93%)) An analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4 g. of sodium hydroxide in 30 ml. of water is added to a solution of 19.4 g. (0.1 mole) of ethyl trans-4-fluorocinnamate (Compound LXV) in 350 ml. of ethanol, and the reaction mixture is stirred at 70° C. for 18 hours. The solvent is evaporated at reduced pressure, and the residue is dissolved in water. The solution is washed once with methyl t-butyl ether and acidified with 6N. hydrochloric acid. The resulting precipitate is washed twice with water and dried to obtain the product (15.5 g. (93%)). An analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C. The solvent is evaporated at reduced pressure the residue is dissolved in water The solution is washed once with methyl t-butyl ether The resulting precipitate is washed twice with water dried to obtain the product (15.5 g. (93%)) An analytical sample was recrystallized from ethyl acetate, m.p. 204°-206° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 9.6 g. of sodium hydride (50% in mineral oil, pentane washed) is added in small portions to a solution of 45 g. of triethyl phosphonoacetate in 400 ml. of dry tetrahydrofuran stirred at 0° C. under nitrogen. The reaction mixture is allowed to warm to room temperature, stirred at room temperature for 1 hour and cooled to 10° C., a solution of 24.8 g. of 4-fluorobenzaldehyde in 25 ml. of dry tetrahydrofuran is adde dropwise, and the reaction mixture is stirred at room temperature for 18 hours, the reaction mixture being maintained under nitrogen throughout. Water is added to the reaction mixture. The reaction mixture is extracted twice with diethyl ether, and the organic layers are combined, dried over anhydrous sodium sulfate and evaporated at reduced pressure to an oil. The oil is distilled at 15 mm. Hg. to obtain the product (28.3 g. (73%)), b.p. 142° C. cooled to 10° C. the reaction mixture is stirred at room temperature for 18 hours the reaction mixture being maintained under nitrogen throughout The reaction mixture is extracted twice with diethyl ether dried over anhydrous sodium sulfate evaporated at reduced pressure to an oil The oil is distilled at 15 mm. Hg to obtain the product (28.3 g. (73%)), b.p. 142° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Trimethylsulfoxonium iodide (7.92 g, 36.0 mmol) in dimethyl sulfoxide (40 mL) was mixed with sodium hydride (55 wt % dispersion in mineral oil, 1.57 g, 36.0 mmol) under cooling with ice, stirred at room temperature for 1 hour and then stirred with (E)-ethyl 3-(4-fluorophenyl)acrylate (5.83 g, 30.0 mmol) for 18 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to give the title compound as a colorless oil (793 mg, yield 13%). under cooling with ice the reaction mixture was extracted with ethyl acetate the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Fluorobenzaldehyde (9.61 g, 80.0 mmol) in tetrahydrofuran (120 mL) was mixed with ethyl 2-(diethoxyphosphoryl)acetate (17.9 g, 80.0 mmol) under cooling with ice, and then sodium ethoxide-ethanol solution (21 wt %, 44.8 mL, 120 mmol) was added dropwise to the reaction mixture under cooling with ice, and the resulting reaction mixture was stirred at room temperature for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→10/1 (v/v)) to give the title compound as a colorless oil (14.1 g, yield 91%). under cooling with ice under cooling with ice the resulting reaction mixture the reaction mixture was extracted with ethyl acetate the organic layer dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→10/1 (v/v))