diethyl 2-(3-methylbut-2-enyl)propanedioate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 70 mg sodium (3.03 mmol) in 1.0 mL absolute ethanol was added 61 mg urea (1.01 mmol), followed by 200 mg of the diethyl prenylmalonate (0.88 mmol) prepared in the previous experiment. The solution was refluxed gently for 12 hours. Most of the ethanol was removed by rotary evaporation, and the residue was diluted in water. The solution was acidified to pH 3 and extracted 2×10 mL with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated to 214 mg of an off-white solid. prepared in the previous experiment The solution was refluxed gently for 12 hours Most of the ethanol was removed by rotary evaporation the residue was diluted in water extracted 2×10 mL with ethyl acetate The combined organic phases were dried over anhydrous magnesium sulfate concentrated to 214 mg of an off-white solid

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 422 mg (14.1 mmol, 80% mineral oil dispersion) sodium hydride was washed 3 ×, each with 5 mL pentane, and suspended in a mixture of 10 mL tetrahydrofuran and 5 mL dimethylformamide. 2.04 g (13.4 mmol) diethyl malonate was added, and the mixture stirred for 40 mins to form a clear light brown solution. Prenyl bromide (2.00 g, 13.4 mmol) was then added, and the solution refluxed for 1 hr. The reaction was quenched with water, acidified to pH 2 with 1N HCl, and extracted 2 ×, each with 10 mL diethyl ether. The organic phases were dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane, furnished 2.734 g of a clear colorless oil in 12 mL fractions 4-16. to form a clear light brown solution the solution refluxed for 1 hr The reaction was quenched with water extracted 2 × The organic phases were dried over MgSO4 filtered concentrated eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane

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

Procedure: 422 mg (14.1 mmol, 80% mineral oil dispersion) sodium hydride was washed 3 ×, each with 5 mL pentane, and suspended in a mixture of 10 mL tetrahydrofuran and 5 mL dimethylformamide. 2.04 g (13.4 mmol) diethyl malonate was added, and the mixture stirred for 40 mins to form a clear light brown solution. Prenyl bromide (2.00 g, 13.4 mmol) was then added, and the solution refluxed for 1 hr. The reaction was quenched with water, acidified to pH 2 with 1N HCl, and extracted 2 ×, each with 10 mL diethyl ether. The organic phases were dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane, furnished 2.734 g of a clear colorless oil in 12 mL fractions 4-16. to form a clear light brown solution the solution refluxed for 1 hr The reaction was quenched with water extracted 2 × The organic phases were dried over MgSO4 filtered concentrated eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane

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

Procedure: 422 mg (14.1 mmol, 80% mineral oil dispersion) sodium hydride was washed 3×, each with 5 mL pentane, and suspended in a mixture of 10 mL tetrahydrofuran and 5 mL dimethylformamide. 2.04 g (13.4 mmol) diethyl malonate was added, and the mixture stirred for 40 mins to form a clear light brown solution. Prenyl bromide (2.00 g, 13.4 mmol) was then added, and the solution refluxed for 1 hr. The reaction was quenched with water, acidified to pH 2 with 1N HCl, and extracted 2×, each with 10 mL diethyl ether. The organic phases were dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane, furnished 2.734 g of a clear colorless oil in 12 mL fractions 4-16. to form a clear light brown solution the solution refluxed for 1 hr The reaction was quenched with water extracted 2× The organic phases were dried over MgSO4 filtered concentrated eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane

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

Procedure: 422 mg (14.1 mmol, 80% mineral oil dispersion) sodium hydride was washed 3×, each with 5 mL pentane, and suspended in a mixture of 10 mL tetrahydrofuran and 5 mL dimethylformamide. 2.04 g (13.4 mmol) diethyl malonate was added, and the mixture stirred for 40 mins to form a clear light brown solution. Prenyl bromide (2.00 g, 13.4 mmol) was then added, and the solution refluxed for 1 hr. The reaction was quenched with water, acidified to pH 2 with 1N HCl, and extracted 2×, each with 10 mL diethyl ether. The organic phases were dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane, furnished 2.734 g of a clear colorless oil in 12 mL fractions 4-16. to form a clear light brown solution the solution refluxed for 1 hr The reaction was quenched with water extracted 2× The organic phases were dried over MgSO4 filtered concentrated eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane

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

Procedure: To a solution of 70 mg sodium (3.03 mmol) in 1.0 mL absolute ethanol was added 61 mg urea (1.01 mmol), followed by 200 mg of the diethyl prenylmalonate (0.88 mmol) prepared in the previous experiment. The solution was refluxed gently for 12 hours. Most of the ethanol was removed by rotary evaporation, and the residue was diluted in water. The solution was acidified to pH 3 and extracted 2×10 mL with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate and concentrated to 214 mg of an off-white solid. prepared in the previous experiment The solution was refluxed gently for 12 hours Most of the ethanol was removed by rotary evaporation the residue was diluted in water extracted 2×10 mL with ethyl acetate The combined organic phases were dried over anhydrous magnesium sulfate concentrated to 214 mg of an off-white solid