3-Chloropropiophenone → 1-Chloro-3-phenylhex-5-en-3-ol

A 1000-mL flask was charged with anhydrous CeCl3 (50 g, 0.2 mol) and THF (360 mL). The mixture was vigorously stirred for 3.5 h at rt. The suspension was then cooled to −78° C., and a solution of allylmagnesium bromide (1.0 M in THF, 200 mL) was added. After stirring for 2 h at −78° C., a solution of 3-chloro-1-phenyl-propan-1-one (25 g, 149 mmol) in THF (269 mL) was added dropwise. The reaction mixture was allowed to slowly warm to rt while stirring overnight. The reaction was then quenched with satd aq NaHCO3, extracted with EtOAc, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 1-chloro-3-phenyl-hex-5-en-3-ol (25 g, 82%) as an oil. 1H NMR (CDCl3): 2.30 (m, 2H), 2.51 (m, 1H), 2.72 (m, 1H), 3.20 (m, 1H), 3.54 (m, 1H), 5.16 (m, 2H), 5.51 (m, 1H), 7.24 (m, 1H), 7.35 (m, 4H).

1. temperatureThe suspension was then cooled to −78° C.
2. stirringAfter stirring for 2 h at −78° C.
3. temperatureto slowly warm to rt
4. stirringwhile stirring overnight
5. customThe reaction was then quenched with satd aq NaHCO3
6. extractionextracted with EtOAc
7. dry with materialdried over Na2SO4
8. customAfter the solvents were evaporated
9. customthe residue was purified by chromatography on silica gel
10. washeluted with hexanes/EtOAc

ORD record

ord-93465cdea8b04d6fa8fecdbfaec511b2

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575156B2