chloromethylsulfanylmethylbenzene

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

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

実験手順: Diethyl isobutylmalonate (22.0 g.) was added to a stirred suspension of sodium hydride (4.8 g. 50% dispersion in oil) in dry toluene (200 ml.), under nitrogen. The mixture was stirred at 80° for one hour. The mixture was cooled and benzyl chloromethyl thioether 5 (16.0 g.) in dry toluene (50 ml.) was added and the mixture was stirred at 80° for two hours. The mixture was cooled and poured into water. The aqueous mixture was extracted into diethyl ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. Diethyl 2-benzylthiomethyl-2-isobutylmalonate (32.0 g.) was obtained as a yellow oil and was used without further purification. The mixture was cooled the mixture was stirred at 80° for two hours The mixture was cooled The aqueous mixture was extracted into diethyl ether The ether extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g

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

実験手順: Diethyl isobutylmalonate (22.0 g.) was added to a stirred suspension of sodium hydride (4.8 g. 50% dispersion in oil) in dry toluene (200 ml.), under nitrogen. The mixture was stirred at 80° for one hour. The mixture was cooled and benzyl chloromethyl thioether 5 (16.0 g.) in dry toluene (50 ml.) was added and the mixture was stirred at 80° for two hours. The mixture was cooled and poured into water. The aqueous mixture was extracted into diethyl ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. Diethyl 2-benzylthiomethyl-2-isobutylmalonate (32.0 g.) was obtained as a yellow oil and was used without further purification. The mixture was cooled the mixture was stirred at 80° for two hours The mixture was cooled The aqueous mixture was extracted into diethyl ether The ether extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo

反応条件: temp:155.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid. prepared was heated The temperature of the oil bath was then raised to 170° C. the volatile materials removed by distillation under reduced pressure The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g