Reaction #165290

Reaction equation

2-(2-nitro-ethyl)-5-phenoxy-pyridine

methanol

sodium bicarbonate

Methylene chloride

lithium methoxide

→

title compound

Yield 69.0%

(5-Phenoxy-pyridin-2-yl)-acetohydroximoyl chloride

Yield 69.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherthe solvent was evaporated under a reduced pressure
2. 2
   workup.ADDITIONwas added at room temperature
3. 3
   workup.STIRRINGwhich was stirred for 10 minutes
4. 4
   Filtrationwas filtered through a Celite pad
5. 5
   Otherthe organic layer was separated
6. 6
   ConcentrationThe organic layer was concentrated under a reduced pressure

Procedure

To 2-(2-nitro-ethyl)-5-phenoxy-pyridine (76 mg, 0.31 mmol) described in Manufacturing Example 121-1-4 and methanol (6.0 mL) was added lithium methoxide (24 mg, 0.62 mmol) at room temperature, which was stirred for 3 minutes, and then the solvent was evaporated under a reduced pressure. Methylene chloride (10 mL) was added to the residue, titanium(IV) chloride (0.11 mL, 1.0 mmol) was added at room temperature, which was stirred for 10 minutes. Cold aqueous sodium bicarbonate and ethyl acetate were added to the reaction solution, which was filtered through a Celite pad, and then the organic layer was separated. The organic layer was concentrated under a reduced pressure to obtain the title compound (56 mg, 69%).

Source