Methanol → (4-(5-Chloro-furan-2-ylmethyl)-phenyl)-acetohydroximoyl chloride

To a mixture of 2-chloro-5-(4-(2-nitro-ethyl)-benzyl)furan (100 mg, 0.38 mmol) described in Manufacturing Example 62-1-5 and methanol (2 mL) was added lithium methoxide (29 mg, 0.75 mmol) at room temperature, which was stirred for 10 minutes at room temperature. The solvent was evaporated from the reaction mixture under a reduced pressure. Titanium (IV) chloride (91 μL, 0.83 mmol) was added at −78° C. to a mixture of the resulting residue, methylene chloride (2 mL) and tetrahydrofuran (1 mL), and stirred for 1 hour at 0° C. The reaction mixture was cooled to −78° C., water (1 mL) was added, and the temperature was gradually raised to room temperature. Ethyl acetate and water were added to extract the reaction mixture. The organic layer was washed with water until the pH became roughly 5. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under a reduced pressure to obtain the title compound (110 mg, 84%).

1. customThe solvent was evaporated from the reaction mixture under a reduced pressure
2. stirringstirred for 1 hour at 0° C
3. temperatureThe reaction mixture was cooled to −78° C.
4. temperaturethe temperature was gradually raised to room temperature
5. extractionto extract the reaction mixture
6. washThe organic layer was washed with water until the pH
7. washThe organic layer was washed with saturated aqueous sodium chloride
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationThe organic layer was concentrated under a reduced pressure

ORD record

ord-9f01ed8c27c842138e89b7244722314f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2