2-diethoxyphosphorylacetaldehyde

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl formylmethylphosphonate (100 g) and ethanol (500 mL). Under a nitrogen atmosphere, the resulting mixture was cooled to 10° C. and (R)-1-(1-naphthyl)ethylamine (85.6 g) was added under stirring. The mixture was left under stirring for an additional hour. The solvent was distilled from this mixture under reduced pressure. The resulting residue (180 g) was used in the next step without additional purification. A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet The mixture was left under stirring for an additional hour The solvent was distilled from this mixture under reduced pressure The resulting residue (180 g) was used in the next step without additional purification

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl formylmethylphosphonate (100 g) and ethanol (500 mL). Under a nitrogen atmosphere, the resulting mixture was cooled to 10° C. and (R)-1-(1-naphthyl)ethylamine (85.6 g) was added under stirring. The mixture was left under stirring for an additional hour. The solvent was distilled from this mixture under reduced pressure. The resulting residue (180 g) was used in the next step without additional purification. A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet The mixture was left under stirring for an additional hour The solvent was distilled from this mixture under reduced pressure The resulting residue (180 g) was used in the next step without additional purification

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl 2,2-diethoxyethylphosphonate (150 g) and water (300 mL), and a slight stream of nitrogen was continuously passed through the system. The resulting mixture was heated to 50° C. and hydrochloric acid (5.6 mL) was added. The mixture was then left under stirring for 4 hours after which water was added and the mixture concentrated under reduced pressure. Sodium chloride was added to the resulting mixture which was then extracted with 4 portions of ethyl acetate. The combined organic phases were distilled under reduced pressure. A 2-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet The mixture was then left was added the mixture concentrated under reduced pressure Sodium chloride was added to the resulting mixture which was then extracted with 4 portions of ethyl acetate The combined organic phases were distilled under reduced pressure

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

Procedure: A mixture consisting of 23 gm (0.03 mol) of erythromycylamine, 10 gm (0.055 mol) of diethylphosphonoacetaldehyde and 300 ml of absolute dioxane was stirred at room temperature for 24 hours. After evaporation of the solvent, the residue was taken up in 150 ml of hot acetonitrile, and the solution was mixed with 750 ml of water. Upon cooling 13 gm (43% of theory) of colorless crystals precipitated, which were dried at 80° C in vacuo. M.p. 110°-113° C (decomp.). After evaporation of the solvent the solution was mixed with 750 ml of water Upon cooling 13 gm (43% of theory) of colorless crystals precipitated which were dried at 80° C in vacuo

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl formylmethylphosphonate (100 g) and ethanol (500 mL). Under a nitrogen atmosphere, the resulting mixture was cooled to 10° C. and (R)-1-(1-naphthyl)ethylamine (85.6 g) was added under stirring. The mixture was left under stirring for an additional hour. The solvent was distilled from this mixture under reduced pressure. The resulting residue (180 g) was used in the next step without additional purification. A 1-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet The mixture was left under stirring for an additional hour The solvent was distilled from this mixture under reduced pressure The resulting residue (180 g) was used in the next step without additional purification

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl 2,2-diethoxyethylphosphonate (150 g) and water (300 mL), and a slight stream of nitrogen was continuously passed through the system. The resulting mixture was heated to 50° C. and hydrochloric acid (5.6 mL) was added. The mixture was then left under stirring for 4 hours after which water was added and the mixture concentrated under reduced pressure. Sodium chloride was added to the resulting mixture which was then extracted with 4 portions of ethyl acetate. The combined organic phases were distilled under reduced pressure. A 2-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet The mixture was then left was added the mixture concentrated under reduced pressure Sodium chloride was added to the resulting mixture which was then extracted with 4 portions of ethyl acetate The combined organic phases were distilled under reduced pressure