thian-4-ylmethanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, a solution of 500 mg (3.78 mmol) of tetrahydrothiopyran-4-ylmethanol in 10 ml of methanol was added with cooling to a solution of 1.86 g (8.70 mmol) of sodium periodate in 18 ml of water. The mixture was stirred at 60° C. for another 1 h, and methanol was then distilled off under reduced pressure and the resulting precipitate was filtered off with suction. The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1, v/v) and, after addition of 5 ml of water, twice with 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Combined yield: 406 mg (65% of theory) methanol was then distilled off under reduced pressure the resulting precipitate was filtered off with suction The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1 v/v) and, after addition of 5 ml of water The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, a solution of 500 mg (3.78 mmol) of tetrahydrothiopyran-4-ylmethanol in 10 ml of methanol was added with cooling to a solution of 1.86 g (8.70 mmol) of sodium periodate in 18 ml of water. The mixture was stirred at 60° C. for another 1 h, and methanol was then distilled off under reduced pressure and the resulting precipitate was filtered off with suction. The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1, v/v) and, after addition of 5 ml of water, twice with 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Combined yield: 406 mg (65% of theory) methanol was then distilled off under reduced pressure the resulting precipitate was filtered off with suction The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1 v/v) and, after addition of 5 ml of water The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, a solution of 500 mg (3.78 mmol) of tetrahydrothiopyran-4-ylmethanol in 10 ml of methanol was added with cooling to a solution of 1.86 g (8.70 mmol) of sodium periodate in 18 ml of water. The mixture was stirred at 60° C. for another 1 h, and methanol was then distilled off under reduced pressure and the resulting precipitate was filtered off with suction. The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1, v/v) and, after addition of 5 ml of water, twice with 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Combined yield: 406 mg (65% of theory) methanol was then distilled off under reduced pressure the resulting precipitate was filtered off with suction The aqueous phase that remained was extracted twice with 10 ml of diethyl ether, twice with 10 ml of dichloromethane, twice with 10 ml of dichloromethane/methanol (1:1 v/v) and, after addition of 5 ml of water The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure The aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran The combined organic phases were dried over sodium sulphate filtered the solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pyridine (7.6 mL, 98.4 mmol) was added at 0° C. to a solution of (tetrahydro-2H-thiopyran-4-yl)methanol (1.3 g, 9.84 mmol) in CH2Cl2 (20 mL) followed by the addition of TsCl (2.0 g, 10.83 mmol). The reaction mixture was stirred at ambient temperature for 18 h, diluted with H2O (200 mL) and extracted with CH2Cl2 (200 mL). Drying over anhydrous Na2SO4 followed by concentration in vacuo gave (tetrahydro-2H-thiopyran-4-yl)methyl 4-methylbenzenesulfonate as an off white solid. The crude was carried forward to the next step without additional purification. Yield (0.75 g, 30%). extracted with CH2Cl2 (200 mL) Drying over anhydrous Na2SO4 followed by concentration in vacuo