2-(4-Chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene → 2-(4-Chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropylethanal
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:9][O:10]C)[C:3]=1[O:15][CH:16]([F:18])[F:17]>C1COCC1.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH:12]2[CH2:13][CH2:14]2)[CH:9]=[O:10])[C:3]=1[O:15][CH:16]([F:18])[F:17]Participants
Procedure
6.00 g of 2-(4-chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI) was dissolved in 60 ml of THF, to which 40 ml of dilute sulfuric acid was added, and the resulting mixture was concentrated at 50° C. under reduced pressure. The resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution, and thereafter, extracted with chloroform. The resulting organic layer was washed with saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 4.51 g of 2-(4-chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropylethanal (XII).
Workup
- additionwas added
- concentrationthe resulting mixture was concentrated at 50° C. under reduced pressure
- additionThe resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution
- extractionextracted with chloroform
- washThe resulting organic layer was washed with saturated salt water
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)
Sources & evidence
- ORD record
- ord-122d66c6356349cab0c445ea555ed804
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525066B2
Reaction notes
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