ethyl 4-cyano-2-oxobutanoate

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

Procedure: A mixture of 7.75 g (0.05 mole) of ethyl 4-cyano-2-oxo-butanoate in 31 g (0.225 mole) of diethyl phosphite is stirred at 20°-30° for 3-4 days. The excess diethyl phosphite is removed on a rotary evaporator under high vacuum at a bath temperature of 50°-700 to yield the crude product as an oil. This is purified by chromatography on silica gel. The excess diethyl phosphite is removed on a rotary evaporator under high vacuum at a bath temperature of 50°-700

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

Procedure: To a solution of 12.8 g (0.10 mole) of ethyl 2-oxo-3-butenoic acid (prepared as in Example 1) in 100 ml of ethanol and 50 ml of water is added 6.5 g (0.10 mole) of potassium cyanide. The mixture is stirred at 30°-50° for about one hour, during which time a solution of 6.0 g (0.10 mole) of acetic acid in 20 ml of ethanol is slowly dripped in. After addition is complete, the mixture is cooled to room temperature and the solvent is removed under vacuum. The residue is partitioned between water and CH2Cl2, the layers separated, and the water extracted further with CH2Cl2. The combined organic layers are dried (Na2SO4) and the solvent is removed to give the crude product. This is purified by flash chromatography on silica gel to give ethyl 4-cyano-2-oxo-butanoate as an oil. After addition the solvent is removed under vacuum The residue is partitioned between water and CH2Cl2 the layers separated the water extracted further with CH2Cl2 The combined organic layers are dried (Na2SO4) the solvent is removed to give the crude product This is purified by flash chromatography on silica gel

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

Procedure: A mixture of 7.75 g (0.05 mole) of ethyl 4-cyano-2-oxo-butanoate in 31 g (0.225 mole) of diethyl phosphite is stirred at 20°-30° for 3-4 days. The excess diethyl phosphite is removed on a rotary evaporator under high vacuum at a bath temperature of 50°-700 to yield the crude product as an oil. This is purified by chromatography on silica gel. The excess diethyl phosphite is removed on a rotary evaporator under high vacuum at a bath temperature of 50°-700

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

Procedure: To a solution of 12.8 g (0.10 mole) of ethyl 2-oxo-3-butenoic acid (prepared as in Example 1) in 100 ml of ethanol and 50 ml of water is added 6.5 g (0.10 mole) of potassium cyanide. The mixture is stirred at 30°-50° for about one hour, during which time a solution of 6.0 g (0.10 mole) of acetic acid in 20 ml of ethanol is slowly dripped in. After addition is complete, the mixture is cooled to room temperature and the solvent is removed under vacuum. The residue is partitioned between water and CH2Cl2, the layers separated, and the water extracted further with CH2Cl2. The combined organic layers are dried (Na2SO4) and the solvent is removed to give the crude product. This is purified by flash chromatography on silica gel to give ethyl 4-cyano-2-oxo-butanoate as an oil. After addition the solvent is removed under vacuum The residue is partitioned between water and CH2Cl2 the layers separated the water extracted further with CH2Cl2 The combined organic layers are dried (Na2SO4) the solvent is removed to give the crude product This is purified by flash chromatography on silica gel