Ethyl (e)-4-(4-nitrophenyl)-4-oxo-2-butenoate (CAS no 131504-53-5), which is also known as , 4-(4-nitrophenyl)-4-oxo-, ethyl ester, (E)-, could be produced through the following synthetic routes.

A. Tributylethynylstannane. An oven-dried, 2-L, three-necked, round-bottomed flask equipped with a mechanical stirrer, a 100-mL addition funnel, and a nitrogen inlet is charged with 24.0 g (0.26 mol) of lithium acetylide-ethylenediamine complex. The system is evacuated, placed under nitrogen, and 800 mL of is added to the system via a cannula. The flask is cooled in an ice-water bath and 70.7 g (0.22 mol) of tributyltin chloride is added dropwise over 45 min. The ice bath is removed and the mixture is stirred for 18 hr at room temperature. The flask is placed in an ice water bath and excess lithium acetylide is hydrolyzed with 20 mL of water. The reaction mixture is concentrated under reduced pressure and washed with hexane (3 × 50 mL). The organic layers are combined and dried over anhydrous magnesium sulfate. Filtration and evaporation of the solvent at reduced pressure gives a colorless oil. Distillation yields 21.4–24.3 g (31–35%) of tributylethynylstannane, bp 90–94°C (0.5 mm) as a water-white liquid.

B. (E)-1,2-Bis(tributylstannyl)ethylene. In a 200-mL, one-necked, round-bottomed flask containing a magnetic stirring bar and a nitrogen inlet are placed 20.6 g (0.066 mol) of tributylethynylstannane, 23.1 g (0.079 mol) of tributyltin hydride, and 0.25 g (0.0016 mol) of 2,2'-azobis(2-methylpropionitrile). The mixture is heated at 90°C with stirring for 6 hr. Distillation (170–186°C, 0.3 mm) yields 35.1–36.6 g (88–92%) of (E)-1,2-bis(tributylstannyl)ethylene as a clear, colorless oil.

C. Ethyl (E)-3-(tributylstannyl)propenoate. A flame-dried, 1-L, three-necked, round-bottomed flask equipped with a magnetic stirring bar, a 100-mL pressure-equalizing addition funnel, and a nitrogen inlet is charged with 26.7 g (0.044 mol) of (E)-1,2-bis(tributylstannyl)ethylene. Tetrahydrofuran (100 mL) is added to the flask by cannula. The system is cooled in a dry ice-acetone bath and the addition funnel is charged, under nitrogen, with 44.8 mL of a 1.2 M solution of methyllithium (0.054 mol) in ethyl ether by means of a double-ended needle. After 10 min the lithium reagent is added dropwise to the flask over a 40-min period. After the addition is complete, the yellow solution is stirred for an additional 2 hr at -78°C during which time a 1-L, one-necked, round-bottomed flask, containing a magnetic stirring bar, is flame-dried under nitrogen. The 1-L, flask, capped with a rubber septum, is charged with a solution of 5.8 g (0.053 mol) of ethyl chloroformate in 150 mL of tetrahydrofuran and cooled to -78°C with a dry ice–acetone bath. Under gentle nitrogen pressure, the metallated reagent is transferred dropwise over a 2.0-hr period by means of a double-ended needle to the 1-L flask containing ethyl chloroformate while the temperature of both flasks is maintained at -78°C. After the addition is complete, the reaction mixture is allowed to stir an additional 30 min at -78°C and then treated with 20 mL of methanol in one portion. After 10 min at -78°C the reaction mixture, while still cold, is transferred to a 1-L separatory funnel containing 200 mL of water and 100 mL of hexane. The organic layer is separated and the aqueous layer is washed with hexane (3 × 50 mL). The combined organic layers are dried over anhydrous sodium sulfate, filtered, and concentrated to give a dark-brown oil. The product is dissolved in hexane (30 mL) and purified by chromatography on a column of silica gel (600 g). Elution is carried out initially with hexane and then with hexane/ethyl acetate (95 : 5). Fractions containing the product are combined to give 10.2 g (59%) of ethyl (E)-3-(tributylstannyl)propenoate as a yellow oil.

D. Ethyl (E)-4-(4-nitrophenyl)-4-oxo-2-butenoate. A flame-dried, 150-mL, one-necked, round-bottomed flask containing a magnetic stirring bar and equipped with a side-arm is charged with 3.20 g (17.2 mmol) of p-nitrobenzoyl chloride, 0.08 g (0.10 mmol) of benzyl(chloro)bis(triphenylphosphine)palladium(II), and 30 mL of chloroform. The bright-yellow solution is evacuated and refilled with carbon monoxide (3 cycles) utilizing a gas bag. After an additional 10 min at room temperature a solution of 8.0 g (20.6 mmol) of ethyl (E)-3-(tributylstannyl)propenoate in 5 mL of chloroform is added to the flask by syringe. The stirring reaction mixture is heated to 50°C for 12 hr while a pressure of 1 atm of carbon monoxide is maintained. The reaction is cooled to room temperature and treated with 18 mL of a 1.2 M solution of pyridinium poly(hydrogen fluoride) along with 10 mL of pyridine. The reaction mixture is allowed to stir at room temperature overnight and then transferred to a 250-mL separatory funnel containing 75 mL of water. After addition of 30 mL of chloroform, the organic layer is washed successively with 10% hydrochloric acid (3 × 20 mL), saturated sodium bicarbonate (3 × 20 mL), water (25 mL), and brine (25 mL). The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated to give a dark-brown solid. The product is dissolved in chloroform and 15 g of silica gel is added to the solution. Concentration under reduced pressure gives a brown powder of silica coated with product, which is immediately placed on the top of a column of silica gel (50 g). Elution is carried out with ethyl acetate and the fractions are combined and concentrated under reduced pressure. The crude product is again placed on a column of silica gel (250 g). Elution is carried out with hexane/ethyl acetate (90 : 10). Fractions containing the product (obtained by collecting the bright yellow band on the column) are combined to give 3.42 g (80%) of ethyl (E)-4-(4-nitrophenyl)-4-oxo-2-butenoate as yellow-green crystals, mp 69–71°C.