Dichloromethane → 4-Benzyloxy-phenyl-acetohydroximoyl chloride

Temperature

10 °C

To a mixture of 1-benzyloxy-4-(2-nitro-ethyl)-benzene described in Manufacturing Example 229-1-2 (39 g, 0.15 mol), tetrahydrofuran (350 mL) and dichloromethane (350 mL) was added n-butyl lithium (63 mL, 2.6 M n-hexane solution, 0.17 mol) at −78° C., which was stirred for 20 minutes at the same temperature. To the reaction mixture was added titanium (IV) chloride (25 mL, 0.23 mol) at the same temperature, and the mixture was warmed gradually to 10° C. After cooling the reaction mixture to 0° C., water (500 mL) and ethyl acetate (700 mL) were added, and the reaction mixture was warmed to room temperature. This organic layer was separated, washed with water (500 mL) and saturated sodium chloride water, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. This residue was filtered with neutral silica gel (ethyl acetate:heptane=1:1), and this filtrate was concentrated under a reduced pressure. The obtained residue was washed with diethyl ether-heptane (1:10) to obtain the title compound (33 g, 78%).

1. temperatureAfter cooling the reaction mixture to 0° C.
2. temperaturethe reaction mixture was warmed to room temperature
3. customThis organic layer was separated
4. washwashed with water (500 mL) and saturated sodium chloride water
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under a reduced pressure
8. filtrationThis residue was filtered with neutral silica gel (ethyl acetate:heptane=1:1)
9. concentrationthis filtrate was concentrated under a reduced pressure
10. washThe obtained residue was washed with diethyl ether-heptane (1:10)

ORD record

ord-d5d36b89ee694b25a5c9579b308284dd

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2