1-chloro-5-phenylpentan-2-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid. m.p. 192-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1). heated at reflux in an atmosphere of dry nitrogen for 4 hours The solution was then evaporated under reduced pressure the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether to give a white solid Recrystallisation of this material from a mixture of dichloromethane and diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C, dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13C10 requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid. m.p. 192-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1). heated at reflux in an atmosphere of dry nitrogen for 4 hours The solution was then evaporated under reduced pressure the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether to give a white solid Recrystallisation of this material from a mixture of dichloromethane and diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C, dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13C10 requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C, dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13C10 requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid, m.p. 192°-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1). heated at reflux in an atmosphere of dry nitrogen for 4 hours The solution was then evaporated under reduced pressure the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether to give a white solid Recrystallisation of this material from a mixture of dichloromethane and diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C., dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2 N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13ClO requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C. was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2 N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C., dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm. Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13ClO requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C. was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid. m.p. 192-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1). heated at reflux in an atmosphere of dry nitrogen for 4 hours The solution was then evaporated under reduced pressure the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether to give a white solid Recrystallisation of this material from a mixture of dichloromethane and diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C, dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13C10 requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled