3-benzyloxolan-2-one

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

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

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

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

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

Procedure: In a 250 mL autoclave a mixture of 2-benzyl-γ-butyrolactone (5.00 g) and Rh-catalyst (5 wt. % Rh on carbon, 0.500 g) in isopropanol (60 mL) was treated with hydrogen (13 bar) at 120° C. for 18 h. Upon completion of the hydrogenation, the mixture was filtered and concentrated on a rotary evaporator to give 4.75 g (92%) of the title compound. Upon completion of the hydrogenation, the mixture was filtered concentrated on a rotary evaporator

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

Procedure: In a 250 mL autoclave a mixture of 2-benzyl-γ-butyrolactone (5.00 g) and Rh-catalyst (5 wt. % Rh on carbon, 0.500 g) in isopropanol (60 mL) was treated with hydrogen (13 bar) at 120° C. for 18 h. Upon completion of the hydrogenation, the mixture was filtered and concentrated on a rotary evaporator to give 4.75 g (92%) of the title compound. Upon completion of the hydrogenation, the mixture was filtered concentrated on a rotary evaporator

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

Procedure: In a 250 mL autoclave a mixture of 2-benzyl-γ-butyrolactone (5.00 g) and Rh-catalyst (5 wt. % Rh on carbon, 0.500 g) in isopropanol (60 mL) was treated with hydrogen (13 bar) at 120° C. for 18 h. Upon completion of the hydrogenation, the mixture was filtered and concentrated on a rotary evaporator to give 4.75 g (92%) of the title compound. Upon completion of the hydrogenation, the mixture was filtered concentrated on a rotary evaporator

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of diisopropylamine (63.0 mL) in THF was treated dropwise with butyl lithium (268 mL of 1.6M solution in hexanes) at −10° C. Upon completion of the addition, the reaction mixture was cooled to −70° C. and then treated dropwise with γ-butyrolactone (33.0 mL) keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After stirring for additional 30 min at −70° C., the mixture was treated dropwise with benzyl bromide (51.0 mL) again keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After completion of the addition, the stirring of the reaction mixture was continued at −70° C. for 2 h. Then the mixture was warmed-up to 0° C. and quenched by addition of a small amount of water. The solvents were removed in vacuum and the residue was redissolved in dichloromethane, washed with 10% aqueous hydrochloric acid, then with water, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 26.0 g (34%) of the title compound. Upon completion of the addition the speed of the addition at such a rate that the temperature of the mixture remained below −60° C the speed of the addition at such a rate that the temperature of the mixture remained below −60° C After completion of the addition the stirring of the reaction mixture was continued at −70° C. for 2 h Then the mixture was warmed-up to 0° C. quenched by addition of a small amount of water The solvents were removed in vacuum the residue was redissolved in dichloromethane washed with 10% aqueous hydrochloric acid with water, dried over magnesium sulfate filtered concentrated on a rotary evaporator distilled in vacuum

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of diisopropylamine (63.0 mL) in THF was treated dropwise with butyl lithium (268 mL of 1.6M solution in hexanes) at −10° C. Upon completion of the addition, the reaction mixture was cooled to −70° C. and then treated dropwise with γ-butyrolactone (33.0 mL) keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After stirring for additional 30 min at −70° C., the mixture was treated dropwise with benzyl bromide (51.0 mL) again keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After completion of the addition, the stirring of the reaction mixture was continued at −70° C. for 2 h. Then the mixture was warmed-up to 0° C. and quenched by addition of a small amount of water. The solvents were removed in vacuum and the residue was redissolved in dichloromethane, washed with 10% aqueous hydrochloric acid, then with water, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 26.0 g (34%) of the title compound. Upon completion of the addition the speed of the addition at such a rate that the temperature of the mixture remained below −60° C the speed of the addition at such a rate that the temperature of the mixture remained below −60° C After completion of the addition the stirring of the reaction mixture was continued at −70° C. for 2 h Then the mixture was warmed-up to 0° C. quenched by addition of a small amount of water The solvents were removed in vacuum the residue was redissolved in dichloromethane washed with 10% aqueous hydrochloric acid with water, dried over magnesium sulfate filtered concentrated on a rotary evaporator distilled in vacuum

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In absolute ethanol (78 ml), α-benzyl-γ-butyrolactone (14 g, 80 mmol) was added and then saturated for thirty minutes with gaseous hydrogen bromide, maintaining the temperature below 50° C. The reaction was then heated to 45° C. and stirred at this temperature for 16 hours. The solution was concentrated under reduced pressure and the resulting oil was taken into ethyl acetate (500 ml), washed once with water, and then dried over magnesium sulfate. The solvents were removed in vacuo to yield 15.13 grams of tan oil. maintaining the temperature below 50° C The solution was concentrated under reduced pressure washed once with water dried over magnesium sulfate The solvents were removed in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (15.18 g, 0.15 mol) in dry tetrahydrofuran (200 ml) at −78° C. under a nitrogen atmosphere, n-butyllithium (1.6 M in hexanes, 94 ml, 0.15 mol) was added dropwise. After twenty minutes of stirring at −78° C., γ-butyrolactone (12.91 g, 0.15 mol) was added dropwise, such that the reaction temperature was maintained below −70° C. After twenty minutes of stirring at −78° C., a mixture of benzyl bromide (25.65 g, 0.15 mol) and hexamethylphosphoramide (26.85 g, 0.15 mol) was added dropwise to the reaction mixture. The reaction mixture was then permitted to warm to −30° C. and stirred at this temperature for two hours. was maintained below −70° C After twenty minutes of stirring at −78° C. was added dropwise to the reaction mixture to warm to −30° C. stirred at this temperature for two hours