3-(3-hydroxypropylsulfanyl)propan-1-ol

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

実験手順: A solution of 3,3′-thiodipropanol (900 mg, 6 mmol) in THF (3 ml) was added dropwise to a suspension of sodium hydride (240 mg, 6 mmol) in THF (15 ml) under an atmosphere of N2. The reaction mixture was stirred at RT for 30 mins, then a solution of tert-butyldimethylsilylchloride (900 mg, 6 mmol) in THF (2 ml) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane to give the title compound as a colourless oil (793 mg). stirring was continued for 16 hours The reaction mixture was partitioned between EtOAc and water The organic layer was separated washed with brine dried (Na2SO4) evaporated in vacuo The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane

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

実験手順: 2.55 g of lithium aluminum hydride are suspended in 100 ml of absolute tetrahydrofuran under argon gasification and treated with a warm solution of 12.0 g of 3,3'-thiodipropionic acid in 100 ml of absolute tetrahydrofuran. After completion of the addition, the resulting heterogenous mixture is heated to reflux for a further 22 hours. After cooling, the mixture is treated with 12.0 ml of saturated potassium carbonate solution, filtered and concentrated. Low-pressure chromatography (0.4 bar) of the resulting colorless oil on silica gel with ethyl acetate and subsequent bulb-tube distillation (150°-170° C./0.15-0.09 mm Hg) gives 2.0 g of 3,3'-thiodi-1-propanol as a colorless, viscous oil; nD23 =1.5088; relative fluorescence: 20 percent for UV excitation, 2 percent for violet excitation, 5 percent for blue excitation. After completion of the addition the resulting heterogenous mixture is heated to reflux for a further 22 hours After cooling filtered concentrated Low-pressure chromatography (0.4 bar) of the resulting colorless oil on silica gel with ethyl acetate and subsequent bulb-tube distillation (150°-170° C./0.15-0.09 mm Hg)

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

実験手順: A solution of 3,3′-thiodipropanol (900 mg, 6 mmol) in THF (3 ml) was added dropwise to a suspension of sodium hydride (240 mg, 6 mmol) in THF (15 ml) under an atmosphere of N2. The reaction mixture was stirred at RT for 30 mins, then a solution of tert-butyldimethylsilylchloride (900 mg, 6 mmol) in THF (2 ml) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane to give the title compound as a colourless oil (793 mg). stirring was continued for 16 hours The reaction mixture was partitioned between EtOAc and water The organic layer was separated washed with brine dried (Na2SO4) evaporated in vacuo The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane

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

実験手順: A solution of 3,3′-thiodipropanol (900 mg, 6 mmol) in THF (3 ml) was added dropwise to a suspension of sodium hydride (240 mg, 6 mmol) in THF (15 ml) under an atmosphere of N2. The reaction mixture was stirred at RT for 30 mins, then a solution of tert-butyldimethylsilylchloride (900 mg, 6 mmol) in THF (2 ml) was added and stirring was continued for 16 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane to give the title compound as a colourless oil (793 mg). stirring was continued for 16 hours The reaction mixture was partitioned between EtOAc and water The organic layer was separated washed with brine dried (Na2SO4) evaporated in vacuo The resulting residue was purified by silica gel chromatography eluting with 20% EtOAc in cyclohexane