4-(4-bromo-2-chlorophenoxy)oxane

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in DCM (250 ml) and then cooled to 0° C. Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to r.t. and shaken for 2 h. The resin was filtered off and washed with DCM. The combined filtrates were evaporated to dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D27 as colorless oil (5.38 g, 95%). Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to r.t. The resin was filtered off washed with DCM The combined filtrates were evaporated to dryness The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%) The desired fractions were collected concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in dichloromethane (250 ml) and then cooled to 0° C. Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to room temperature and shaken for 2 hours. The resin was filtered off and washed with dichloromethane. The combined filtrates were evaporated till dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2%). The desired fractions were collected and evaporated in vacuo to yield intermediate 14 as a colorless oil (5.38 g, 95%). Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to room temperature The resin was filtered off washed with dichloromethane The combined filtrates were evaporated till dryness The crude product thus obtained was purified by column chromatography (silica gel The desired fractions were collected evaporated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in dichloromethane (250 ml) and then cooled to 0° C. Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to room temperature and shaken for 2 hours. The resin was filtered off and washed with dichloromethane. The combined filtrates were evaporated till dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2%). The desired fractions were collected and evaporated in vacuo to yield intermediate 14 as a colorless oil (5.38 g, 95%). Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to room temperature The resin was filtered off washed with dichloromethane The combined filtrates were evaporated till dryness The crude product thus obtained was purified by column chromatography (silica gel The desired fractions were collected evaporated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in DCM (250 ml) and then cooled to 0° C. Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to r.t. and shaken for 2 h. The resin was filtered off and washed with DCM. The combined filtrates were evaporated to dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D27 as colorless oil (5.38 g, 95%). Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to r.t. The resin was filtered off washed with DCM The combined filtrates were evaporated to dryness The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%) The desired fractions were collected concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in dichloromethane (250 ml) and then cooled to 0° C. Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to room temperature and shaken for 2 hours. The resin was filtered off and washed with dichloromethane. The combined filtrates were evaporated till dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM to DCM/MeOH(NH3) up to 2%). The desired fractions were collected and evaporated in vacuo to yield intermediate 14 as a colorless oil (5.38 g, 95%). Di-tent-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to room temperature The resin was filtered off washed with dichloromethane The combined filtrates were evaporated till dryness The crude product thus obtained was purified by column chromatography (silica gel The desired fractions were collected evaporated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-bromo-2-chloro-phenol (4 g, 19.28 mmol), tetrahydro-4-pyranol (2.20 ml, 23.13 mmol) and polymer supported triphenylphosphine (17.29 g, 39.29 mmol; purchased from Argonaut, loading 2.23 mmol/g) was suspended in DCM (250 ml) and then cooled to 0° C. Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise and the reaction mixture was warmed to r.t. and shaken for 2 h. The resin was filtered off and washed with DCM. The combined filtrates were evaporated to dryness. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D27 as colorless oil (5.38 g, 95%). Di-tert-butyl azadicarboxylate (6.65 g, 28.92 mmol) was added portionwise the reaction mixture was warmed to r.t. The resin was filtered off washed with DCM The combined filtrates were evaporated to dryness The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2%) The desired fractions were collected concentrated in vacuo