1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl chloride → (2-(Fluoromethyl)-1,3-dioxan-2-yl)methyl benzoate

To a toluene (100 ml) solution of (2-(hydroxymethyl)-1,3-dioxan-2-yl)methyl benzoate (4.76 g, 18.8 mmol), 1,8-diazabicyclo[5.4.0]unedec-7-ene (8.43 ml, 56.4 mmol) was added, cooled on ice and nonafluoro-1-butanesulfonyl chloride (5.06 ml, 28.2 mmol) was added. The mixture was stirred under ice-cool for 15 minutes, and at 40° C. for 20 hours, and further stirred at room temperature for 8 days. The reaction mixture was extracted by adding water and ethyl acetate. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, and filtrated through silica gel, and then, the filtrate was concentrated. The residue was subjected twice to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=4/1) to obtain the title compound (2.22 g, yield: 46.4%).

1. additionwas added
2. temperaturecool for 15 minutes
3. stirringfurther stirred at room temperature for 8 days
4. extractionThe reaction mixture was extracted
5. additionby adding water and ethyl acetate
6. washThe organic layer was washed with a saturated saline solution
7. dry with materialdried over magnesium sulfate
8. filtrationfiltrated through silica gel
9. concentrationthe filtrate was concentrated
10. washThe residue was subjected twice to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=4/1)

ORD record

ord-642688a9588640ef9be8a3682d8ff719

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124780B2