Methyl iodide → HCID 90060301, compound

Under a nitrogen atmosphere, 60% sodium hydride (2.08 g, 52 mmol) was suspended in anhydrous toluene (75 mL). In a different flask, tert-butyl 1,3-dithiane-2-carboxylate (10 g, 45.4 mmol) and iodomethane (3.0 mL, 47.7 mmol) were dissolved in N,N-dimethylformamide (35 mL), and the solution was added dropwise to the first flask at room temperature. After the dropwise addition, the mixture was stirred at room temperature for further 2 hours. The progress of the reaction was then stopped by adding a saturated aqueous solution of ammonium chloride. The mixture was extracted with a mixture (1:1 v/v, 200 mL) of n-hexane and ethyl acetate. The separated organic layer was washed twice with water, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain quantitatively the target compound as white solid.

1. additionthe solution was added dropwise to the first flask at room temperature
2. additionAfter the dropwise addition
3. extractionThe mixture was extracted with a mixture (1:1 v/v, 200 mL) of n-hexane and ethyl acetate
4. washThe separated organic layer was washed twice with water
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

ORD record

ord-6df449eb2fa742c48aaddeb935124f70

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2