Dichloromethane → 4-Butoxymethyl-phenyl-acetohydroximoyl chloride

To a solution of 1-butoxymethyl-4-(2-nitroethyl)-benzene (55 mg, 0.23 mmol) described in Manufacturing Example 4-1-3 in methanol (2 mL) was added sodium methoxide (1.49 M methanol solution, 47.3 μl, 0.23 mmol) at 0° C. The reaction solution was stirred for 35 minutes at room temperature, and concentrated under a reduced pressure. To a solution of the residue in methylene chloride (2 mL) was added titanium (IV) chloride (28 μL, 0.23 mmol) under nitrogen atmosphere at −78° C., which was then stirred for 30 minutes at 0° C. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the magnesium sulfate was removed by filtration. The organic layer was filtered with silica gel, and the filtrate was evaporated under a reduced pressure to obtain the title compound (59 mg, 99%) as a crude product.

1. concentrationconcentrated under a reduced pressure
2. stirringwhich was then stirred for 30 minutes at 0° C
3. customThe reaction solution was partitioned into water and ethyl acetate at 0° C
4. washThe organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe magnesium sulfate was removed by filtration
7. filtrationThe organic layer was filtered with silica gel
8. customthe filtrate was evaporated under a reduced pressure

ORD record

ord-1a51d7cca76a44b3ac52ac0977b00ad2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2