Cyclobutylmethyl methanesulfonate

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1,2,4-triazole-3-thiol (20.2 g; 0.20 mol) and sodium methoxide (11.8 g; 0.22 mol) in methanol (250 ml) is added cyclobutylmethyl methanesulfonate (36.4 g; 0.22 mol). The mixture was refluxed for 27 h under dry nitrogen, allowed to cool to 25° C. and filtered. The solid was washed with ethyl acetate and the organic solutions combined and evaporated. The residue was dissolved in water (250 ml) and extracted into ethyl acetate (250 ml) and dichloromethane (100 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated to afford crude cyclobutylmethyl 1,2,4-triazol-3-yl sulfide (21.8 g; 65%) as a white, sticky solid. NMR -d(CDCl3 ; 60 MHz) 1.5-2.8 (m), 3.2 (2H, d, J=7 Hz), 8.0 (1H, s) and 12.4 (1H, br s). The mixture was refluxed for 27 h under dry nitrogen filtered The solid was washed with ethyl acetate evaporated The residue was dissolved in water (250 ml) extracted into ethyl acetate (250 ml) and dichloromethane (100 ml) dried (Na2SO4) filtered evaporated

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

実験手順: Cyclobutanemethanol (24.9 g; 0.287 mol) and methanesulfonyl chloride (35.3 g; 0.302 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (44 ml; 0.32 mol) was added dropwise over 15 min with external cooling so that the reaction temperature remained below -5° C. The reaction mixture was allowed to warm to room temperature over 1 h and then filtered. The remaining solid was washed with ether. The ether solutions were combined and the ether evaporated, to afford crude cyclobutylmethyl methanesulfonate (48.75 g) as a pale yellow liquid, which was used in the next step without further purification. NMR - d(CDCl3 ; 60 MHz) 1.6-2.9 (7H, m), 3.0 (3H, s) and 4.1 (2H, d, J=7 Hz). with external cooling so that the reaction temperature remained below -5° C filtered The remaining solid was washed with ether the ether evaporated

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

実験手順: Cyclobutanemethanol (24.9 g; 0.287 mol) and methanesulfonyl chloride (35.3 g; 0.302 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (44 ml; 0.32 mol) was added dropwise over 15 min with external cooling so that the reaction temperature remained below -5° C. The reaction mixture was allowed to warm to room temperature over 1 h and then filtered. The remaining solid was washed with ether. The ether solutions were combined and the ether evaporated, to afford crude cyclobutylmethyl methanesulfonate (48.75 g) as a pale yellow liquid, which was used in the next step without further purification. NMR - d(CDCl3 ; 60 MHz) 1.6-2.9 (7H, m), 3.0 (3H, s) and 4.1 (2H, d, J=7 Hz). with external cooling so that the reaction temperature remained below -5° C filtered The remaining solid was washed with ether the ether evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1,2,4-triazole-3-thiol (20.2 g; 0.20 mol) and sodium methoxide (11.8 g; 0.22 mol) in methanol (250 ml) is added cyclobutylmethyl methanesulfonate (36.4 g; 0.22 mol). The mixture was refluxed for 27 h under dry nitrogen, allowed to cool to 25° C. and filtered. The solid was washed with ethyl acetate and the organic solutions combined and evaporated. The residue was dissolved in water (250 ml) and extracted into ethyl acetate (250 ml) and dichloromethane (100 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated to afford crude cyclobutylmethyl 1,2,4-triazol-3-yl sulfide (21.8 g; 65%) as a white, sticky solid. NMR -d(CDCl3 ; 60 MHz) 1.5-2.8 (m), 3.2 (2H, d, J=7 Hz), 8.0 (1H, s) and 12.4 (1H, br s). The mixture was refluxed for 27 h under dry nitrogen filtered The solid was washed with ethyl acetate evaporated The residue was dissolved in water (250 ml) extracted into ethyl acetate (250 ml) and dichloromethane (100 ml) dried (Na2SO4) filtered evaporated

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

実験手順: Cyclobutanemethanol (24.9 g; 0.287 mol) and methanesulfonyl chloride (35.3 g; 0.302 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (44 ml; 0.32 mol) was added dropwise over 15 min with external cooling so that the reaction temperature remained below -5° C. The reaction mixture was allowed to warm to room temperature over 1 h and then filtered. The remaining solid was washed with ether. The ether solutions were combined and the ether evaporated, to afford crude cyclobutylmethyl methanesulfonate (48.75 g) as a pale yellow liquid, which was used in the next step without further purification. NMR - d(CDCl3 ; 60 MHz) 1.6-2.9 (7H, m), 3.0 (3H, s) and 4.1 (2H, d, J=7 Hz). with external cooling so that the reaction temperature remained below -5° C filtered The remaining solid was washed with ether the ether evaporated