2-Bromoethyl methyl ether → Tert-butyl 2-(2-methoxyethyl)-1,3-dithiane-2-carboxylate

A solution of tert-butyl[1,3]dithiane-2-carboxylate (2 g, 9.08 mmol) in THF (16 mL) was cooled to −78° C., and a solution of n-butyllithium (1.58 M in Hexane, 8.62 mL, 13.6 mmol) was added. After stirring for 1 hour, 2-bromoethyl methyl ether (1.70 mL, 18.1 mmol) was added. After stirring at −78° C. for 15 minutes, the cooling bath was removed, and, while allowing the temperature to gradually return to room temperature, the solution was stirred at room temperature for 16 hours. After confirming the consumption of the starting materials by LCMS, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine, and subsequently dried over anhydrous sodium sulfate. The organic layer was filtered, and the solvent was distilled off. The resulting residue was purified with SP1 (SiO2 cartridge) to obtain tert-butyl 2-(2-methoxy-ethyl)-[1,3]dithiane-2-carboxylate (1.75 g, 69% yield).

1. stirringAfter stirring at −78° C. for 15 minutes
2. customthe cooling bath was removed
3. customto gradually return to room temperature
4. stirringthe solution was stirred at room temperature for 16 hours
5. customthe consumption of the starting materials by LCMS
6. additiona saturated aqueous solution of ammonium chloride was added
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was sequentially washed with water
9. dry with materiala saturated brine, and subsequently dried over anhydrous sodium sulfate
10. filtrationThe organic layer was filtered
11. distillationthe solvent was distilled off
12. customThe resulting residue was purified with SP1 (SiO2 cartridge)

ORD record

ord-31833b91e05c4dc6861a35a2f86f687c

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2