N,N-Diethylethanamine trihydrofluoride → HCID 90389316, compound

To a solution of triethylamine trihydrofluoride (Aldrich, 1.9 mL, 12 mmol) in DCM (30 mL) at −78° C., was added Xtalfluor-E (4.1 g, 18 mmol, Aldrich), followed by a solution of (5-chloro-2-vinylpyridin-3-yl)methanol (2 g, 12 mmol) in DCM (40 mL). The cold bath was removed and the reaction mixture was allowed to warm from −78° C. to rt over a period of 15 min. The reaction was quenched by the addition of aqueous saturated bicarbonate solution. After 15 min stirring at rt, the reaction mixture was diluted with EtOAc and water. The organic phase was separated and dried over MgSO4. The filtrate was absorbed onto a plug of silica gel and purified by chromatography through, eluting with a gradient of 5% to 45% EtOAc in hexane, to provide the title compound as colorless oil (1.22 g). LC/MS m/z=172.1 [M+H]+.

1. customThe cold bath was removed
2. temperatureto warm from −78° C. to rt over a period of 15 min
3. customThe reaction was quenched by the addition of aqueous saturated bicarbonate solution
4. additionthe reaction mixture was diluted with EtOAc and water
5. customThe organic phase was separated
6. dry with materialdried over MgSO4
7. customThe filtrate was absorbed onto a plug of silica gel
8. custompurified by chromatography through,
9. washeluting with a gradient of 5% to 45% EtOAc in hexane

ORD record

ord-18f5386b254347b5b7c9b197e5820ce4

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2