Water → 4-(Hydroxymethyl)-1lambda6-thiane-1,1-dione

Temperature

60 °C

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)

1. distillationmethanol was then distilled off under reduced pressure
2. filtrationthe resulting precipitate was filtered off with suction
3. extractionThe 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
4. additionv/v) and, after addition of 5 ml of water
5. dry with materialThe combined organic phases were dried over sodium sulphate
6. filtrationfiltered
7. customthe solvent was removed under reduced pressure
8. extractionThe aqueous phase was extracted four more times with 20 ml of 2-methyltetrahydrofuran
9. dry with materialThe combined organic phases were dried over sodium sulphate
10. filtrationfiltered
11. customthe solvent was removed under reduced pressure

ORD record

ord-658bfb522468462189e71b811dfc540d

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434690B2