Diethyl Ether → 1-(6-Chloropyridin-2-yl)propan-1-ol

Temperature

-78 °C

To a solution of 6-chloropicolinaldehyde (1.00 g, 7.06 mmol) in 20 mL of THF at −78° C. was added ethylmagnesium bromide, 3.0 M solution in diethyl ether (3.53 mL, 10.60 mmol) slowly. The reaction mixture was stirred at −78° C. for 2 h. The reaction mixture was quenched with sat'd NH4Cl aqueous solution, and extracted with ether (3×100 mL). The combined organic layers were dried over Na2SO4 and evaporated to provide the crude product. The crude product was purified by chromatography on silica gel, eluting with 10 to 60% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=172 (M+1).

1. customThe reaction mixture was quenched with sat'd NH4Cl aqueous solution
2. extractionextracted with ether (3×100 mL)
3. dry with materialThe combined organic layers were dried over Na2SO4
4. customevaporated
5. customto provide the crude product
6. customThe crude product was purified by chromatography on silica gel
7. washeluting with 10 to 60% EtOAc/hexane

ORD record

ord-d171b6432680426398a6b38577199092

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2