(Diethylamino)sulfur trifluoride → HCID 90389342, compound

Temperature

-78 °C

To a solution of (5-(chloromethyl)-4,5-dihydroisoxazol-3-yl)methanol (1.58 g, 10.56 mmol, 6a rac, Tetrahedron 1986, 42, 5267) in DCM (30 mL) at −78° C. was added (diethylamino)sulfur trifluoride (1.60 ml, 12.11 mmol). The reaction mixture was stirred at −78° C. for 10 min, warmed from −78° C. to room temperature over 15 min, stirred at room temperature for 1 h and quenched with saturated aq. saturated NaHCO3 solution. The reaction mixture was diluted with diethyl ether and water. The aqueous phase was extracted with diethyl ether (4×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo to give a dark red oil. Purification by flash column chromatography on silica gel (20% diethyl ether in pentane) gave the title compound (0.79 g, 49% yield).

1. temperaturewarmed from −78° C. to room temperature over 15 min
2. stirringstirred at room temperature for 1 h
3. customquenched with saturated aq. saturated NaHCO3 solution
4. additionThe reaction mixture was diluted with diethyl ether and water
5. extractionThe aqueous phase was extracted with diethyl ether (4×)
6. washthe combined organic extracts were washed with brine (1×)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a dark red oil
11. customPurification by flash column chromatography on silica gel (20% diethyl ether in pentane)

ORD record

ord-d8e0a3db4b41490c923ba3ca16b294a9

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2