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

5.54 g of (methoxymethyl) triphenyl phosphonium chloride is suspended in 53 ml of anhydrous ether and 18.4 ml of phenyllithium (0.88 M) was dropped thereto and the resulting mixture was stirred at a room temperature for 15 minutes. 35 ml of ether solution of 3.01 g of (4-chloro-3-methyl-2-pyridyl)cyclopropylketone (X) was dropped thereto and the resulting mixture was stirred at a room temperature for 2 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-methyl-2-pyridyl)-2-cyclopropyl-1-methoxyethene.

1. stirringthe resulting mixture was stirred at a room temperature for 2 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-e61ff8f32b97474db61a3560936f9e6e

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525066B2