Methoxymethyl-triphenylphosphonium chloride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine

18.27 g of (methoxymethyl) triphenyl phosphonium chloride is suspended in 200 ml of anhydrous ether, 51.3 ml of phenyllithium (1.04 M) was dropped and the resulting mixture was stirred at a room temperature for 15 minutes. 145 ml of ether solution of 12.57 g of (4-chloro-3-difluoromethoxy-2-pyridyl)cyclopropylketone (X) was dropped to the mixture, which was stirred at a room temperature for 12 hours. The resulting residue was separated by filtering and washed with ether, and thereafter, the ether filtrate and ether used for washing were collected together and the collected solution was washed with 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 1.66 g of 2-(4-chloro-3-difluomethoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI).

1. stirringwas stirred at a room temperature for 12 hours
2. customThe resulting residue was separated
3. filtrationby filtering
4. washwashed with ether
5. washfor washing
6. customwere collected together
7. washthe collected solution was washed with water
8. dry with materialdried over anhydrous sodium sulfate
9. distillationthe solvent was distilled off under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

ORD record

ord-448f7aa3506d4a78a2bde0a420ab2074

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525066B2