ethyl 4-diethoxyphosphoryl-3-oxobutanoate

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

Procedure: The title compound of Example 7 (17 g, 63.8 mmol) was dissolved in 200 mL of methanol. To this solution was added PtO2 (1.7 g, 10% w/w). The mixture was degassed by evacuation of air, then refilling with hydrogen. This degassing procedure was repeated three times. The pressure in the Parr-shaker was set to 50 psi, and the mixture was shaken for 36 hours. The catalyst was filtered through a Celite pad and the filtrate was concentrated on a rotavap to give 17.3 g (~100%) of the title compound as a white solid, m.p. 33° C. to 35° C. The mixture was degassed by evacuation of air The catalyst was filtered through a Celite pad the filtrate was concentrated on a rotavap

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

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

Procedure: The title compound of Example 7 (17 g, 63.8 mmol) was dissolved in 200 mL of methanol. To this solution was added PtO2 (1.7 g, 10% w/w). The mixture was degassed by evacuation of air, then refilling with hydrogen. This degassing procedure was repeated three times. The pressure in the Parr-shaker was set to 50 psi, and the mixture was shaken for 36 hours. The catalyst was filtered through a Celite pad and the filtrate was concentrated on a rotavap to give 17.3 g (~100%) of the title compound as a white solid, m.p. 33° C. to 35° C. The mixture was degassed by evacuation of air The catalyst was filtered through a Celite pad the filtrate was concentrated on a rotavap

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)

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

Procedure: The title compound of Example 7 (17 g, 63.8 mmol) was dissolved in 200 mL of methanol. To this solution was added PtO2 (1.7 g, 10% w/w). The mixture was degassed by evacuation of air, then refilling with hydrogen. This degassing procedure was repeated three times. The pressure in the Parr-shaker was set to 50 psi, and the mixture was shaken for 36 hours. The catalyst was filtered through a Celite pad and the filtrate was concentrated on a rotavap to give 17.3 g (~100%) of the title compound as a white solid, m.p. 33° C. to 35° C. The mixture was degassed by evacuation of air The catalyst was filtered through a Celite pad the filtrate was concentrated on a rotavap

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title A compound of Example 3 (41.0 g, 0.174 mol) was dissolved in (EtO)3P (150 mL, 0.87 mol) and heated at 115° C. (bath temperature) for 18 hours and then cooled to room temperature. The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature). The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9), to give the title compound as a pale yellow liquid (31 g, 67%). cooled to room temperature The excess (EtO)3P was distilled off at reduced pressure (1 mm Hg, 45° C. bath temperature) The resulting brown residue was purified by chromatography on silica gel, isopropanol:hexane (1:9)