Triethylamine → Oxolan-3-yl methanesulfonate

Temperature

0 °C

3-Hydroxytetrahydrofuran (83.3 μL, 1.03 mmol) was dissolved in methylene chloride (anhydrous, 2 mL) and cooled to 0° C. followed by the addition of triethylamine (166 μL, 1.2 mmol) and methanesulfonyl chloride (88 μL, 1.14 mmol). The reaction mixture was stirred for 16 h while gradually warming to ambient temperature. The reaction was quenched with water, diluted with methylene chloride (20 mL), and the resulting layers were separated. The organic layer was washed with water (2×2 mL) and the combined aqueous phases were extracted with methylene chloride (2×3 mL). The combined organic phases were washed with brine (2×2 mL), dried over Na2SO4, filtered, and concentrated. The crude product was used directly in the next step.

1. temperaturewhile gradually warming to ambient temperature
2. customThe reaction was quenched with water
3. additiondiluted with methylene chloride (20 mL)
4. customthe resulting layers were separated
5. washThe organic layer was washed with water (2×2 mL)
6. extractionthe combined aqueous phases were extracted with methylene chloride (2×3 mL)
7. washThe combined organic phases were washed with brine (2×2 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-51df0bc103b84e5e881ac80e73e6e14c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767675B2