1,3-Dithiane → HCID 12102453, compound

Temperature

-30 °C

A solution containing 1,3-dithiane (11 g) in THF (190 mL) was cooled to −70° C. n-Butyllithium (2.64 M solution in hexane, 35 mL) was added to the reaction solution, and then the mixture was heated to −30° C. and stirred for one hour. The reaction solution was cooled to −70° C., and a solution containing benzyl (R)-(−)-glycidyl ether (16.5 g) in THF (18 mL) was added dropwise. The cooling bath was removed and the mixture was gradually warmed to room temperature. After stirring overnight, a saturated ammonium chloride solution, brine and t-butyl methyl ether were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure to obtain a residue. The residue was subjected to silica gel column chromatography to obtain the title compound (22.1 g).

1. additionwas added to the reaction solution
2. temperatureThe reaction solution was cooled to −70° C.
3. additionwas added dropwise
4. customThe cooling bath was removed
5. temperaturethe mixture was gradually warmed to room temperature
6. stirringAfter stirring overnight
7. additiona saturated ammonium chloride solution, brine and t-butyl methyl ether were added to the reaction solution
8. customthe organic layer was separated
9. washThe organic layer was washed with brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe drying agent was removed by filtration
12. concentrationthe filtrate was concentrated under reduced pressure
13. customto obtain a residue

ORD record

ord-360d68c1a4804ce293d82e412040a660

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946210B2