Ethyl Acetate → 1-(4-Cyclohexyloxy-phenyl)hexan-2-one

To a stirred solution of the 2-(4-cyclohexyloxy-phenyl)-N-methoxy-N-methyl-acetamide (149 mmol, 41.4 g) in anhydrous THF (150 mL) at −78° C. was added n-butyl lithium (1.6 M in hexanes, 298 mmol, 186 mL) dropwise over 45 minutes. The dry ice/acetone bath was replaced with an ice bath, and the reaction was stirred for an additional 30 min. TLC (30% ethyl acetate in hexanes) analysis indicated complete consumption of starting material. The reaction mixture was quenched by addition of saturated ammonium chloride (100 mL) at 0° C., further diluted with water (125 mL) and extracted with ethyl acetate (2×150 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was dissolved in 6% ethyl acetate in hexanes and filtered through a 110 g SiO2 column. The column was eluted with 6% ethyl acetate in hexanes to provide 1-(4-cyclohexyloxy-phenyl)hexan-2-one upon evaporation of solvent.

1. customconsumption of starting material
2. customThe reaction mixture was quenched by addition of saturated ammonium chloride (100 mL) at 0° C.
3. additionfurther diluted with water (125 mL)
4. extractionextracted with ethyl acetate (2×150 mL)
5. washThe combined ethyl acetate layers were washed with brine (100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. dissolutionThe residue was dissolved in 6% ethyl acetate in hexanes
10. filtrationfiltered through a 110 g SiO2 column
11. washThe column was eluted with 6% ethyl acetate in hexanes

ORD-Eintrag

ord-3671b1d188674fa8a744f68de4b3a9f0

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08741900B2