(2-ethoxy-2-oxoethyl)phosphonic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 100 ml. of absolute ethanol was placed 28 g. (0.2 mole) of phosphonoacetic acid. The solution was treated with a stream of dry hydrogen chloride at 0° C. for 45 minutes. After refluxing for 3 hours the solution was allowed to stand overnight at room temperature. Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH. After refluxing for 3 hours the solution Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL RB flask fitted with magnetic stirrer was charged with 160 mL of tetrahydrofuran. To the stirred solvent was added ethyl phosphonoacetate (16.5 g, 73.6 mmol) under argon atmosphere. The reaction mixture was cooled to 0° C. and sodium hydride (2.65 g, 110 mmol) was added portion wise, stirred for 15 minutes at the same temperature. Then 4-methoxybenzaldehyde (5 g, 36.0 mmol) in tetrahydrofuran (30 mL) was added drop wise. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with water at 0° C. by slow addition, stirred for 10 minutes. The layers were separated; ethyl acetate (50 mL) was added to the aqueous layer and extracted the layers. The organic layer was washed with brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow semi-solid (7.4 g, yield: 98.76%). 1H NMR (300 MHz, CDCl3): δ 7.54-7.60 (d, 1H), 7.39-7.42 (d, 2H), 6.82-6.85 (d, 2H), 6.21-6.26 (d, 1H), 4.15-4.22 (q, 2H), 3.76 (s, 3H), 1.24-1.28 (t, 3H). To a 500 mL RB flask fitted with magnetic stirrer The reaction mixture was stirred at 0° C. for 1 h The reaction mixture was quenched with water at 0° C. by slow addition stirred for 10 minutes The layers were separated ethyl acetate (50 mL) was added to the aqueous layer extracted the layers The organic layer was washed with brine solution (50 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL RB flask fitted with magnetic stirrer was charged with 160 mL of tetrahydrofuran. To the stirred solvent was added ethyl phosphonoacetate (16.5 g, 73.6 mmol) under argon atmosphere. The reaction mixture was cooled to 0° C. and sodium hydride (2.65 g, 110 mmol) was added portion wise, stirred for 15 minutes at the same temperature. Then 4-methoxybenzaldehyde (5 g, 36.0 mmol) in tetrahydrofuran (30 mL) was added drop wise. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with water at 0° C. by slow addition, stirred for 10 minutes. The layers were separated; ethyl acetate (50 mL) was added to the aqueous layer and extracted the layers. The organic layer was washed with brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow semi-solid (7.4 g, yield: 98.76%). 1H NMR (300 MHz, CDCl3): δ 7.54-7.60 (d, 1H), 7.39-7.42 (d, 2H), 6.82-6.85 (d, 2H), 6.21-6.26 (d, 1H), 4.15-4.22 (q, 2H), 3.76 (s, 3H), 1.24-1.28 (t, 3H). To a 500 mL RB flask fitted with magnetic stirrer The reaction mixture was stirred at 0° C. for 1 h The reaction mixture was quenched with water at 0° C. by slow addition stirred for 10 minutes The layers were separated ethyl acetate (50 mL) was added to the aqueous layer extracted the layers The organic layer was washed with brine solution (50 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 100 ml. of absolute ethanol was placed 28 g. (0.2 mole) of phosphonoacetic acid. The solution was treated with a stream of dry hydrogen chloride at 0° C. for 45 minutes. After refluxing for 3 hours the solution was allowed to stand overnight at room temperature. Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH. After refluxing for 3 hours the solution Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-O-octadecyl-2,2-dimethoxy-1,3-propanediol (1.92 gm, 5 mmol) and ethyl phosphonoformate (1.19 g, 5 mmol) in dry pyridine (50 mL), cooled in an ice-salt bath, was added a solution of N,N-dicyclohexylcarbodiimide (3.1 g, 15 mmol) in dry dichloromethane (20 mL). The resulting mixture was stirred at room temperature over. The mixture was filtered, and the filtrate was concentrated to dryness. The residue was flash chromatographed with a gradient of 0-10% methanol in dichloromethane to give the target compound. In a similar manner, use of ethyl phosphono-acetate resulted in the corresponding 1-O-octadecyl-2,2-dimethoxy-1,3-propane diol-3-ethylphosphonoacetate. The mixture was filtered the filtrate was concentrated to dryness chromatographed with a gradient of 0-10% methanol in dichloromethane to give the target compound

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL RB flask fitted with magnetic stirrer was charged with 160 mL of tetrahydrofuran. To the stirred solvent was added ethyl phosphonoacetate (16.5 g, 73.6 mmol) under argon atmosphere. The reaction mixture was cooled to 0° C. and sodium hydride (2.65 g, 110 mmol) was added portion wise, stirred for 15 minutes at the same temperature. Then 4-methoxybenzaldehyde (5 g, 36.0 mmol) in tetrahydrofuran (30 mL) was added drop wise. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with water at 0° C. by slow addition, stirred for 10 minutes. The layers were separated; ethyl acetate (50 mL) was added to the aqueous layer and extracted the layers. The organic layer was washed with brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow semi-solid (7.4 g, yield: 98.76%). 1H NMR (300 MHz, CDCl3): δ 7.54-7.60 (d, 1H), 7.39-7.42 (d, 2H), 6.82-6.85 (d, 2H), 6.21-6.26 (d, 1H), 4.15-4.22 (q, 2H), 3.76 (s, 3H), 1.24-1.28 (t, 3H). To a 500 mL RB flask fitted with magnetic stirrer The reaction mixture was stirred at 0° C. for 1 h The reaction mixture was quenched with water at 0° C. by slow addition stirred for 10 minutes The layers were separated ethyl acetate (50 mL) was added to the aqueous layer extracted the layers The organic layer was washed with brine solution (50 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 100 ml. of absolute ethanol was placed 28 g. (0.2 mole) of phosphonoacetic acid. The solution was treated with a stream of dry hydrogen chloride at 0° C. for 45 minutes. After refluxing for 3 hours the solution was allowed to stand overnight at room temperature. Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH. After refluxing for 3 hours the solution Evaporation of the solvent yielded a viscous oil, which was dried in vacuo over P2O5 and NaOH