Hexane → HCID 54115416, compound

Temperature

-20 °C

Under a nitrogen atmosphere, 33.6 ml of n-butyllithium/hexane solution (1.2M solution) was added to a solution of 17.3 g of methoxymethyltriphenylphosphonium chloride in 150 ml of dry THF at -60° C. The reaction solution was stirred at -60° C. for 30 minutes and at -20° C. for 30 minutes. A solution of 7.0 g of 4-chloro-α,α,α-trifluoroacetophenone in 10 ml of dry THF was slowly added to the reaction solution at -60° C. The reaction solution was stirred at -60° C. for 1 hour and at room temperature for 12 hours. Thereafter, 200 ml of n-hexane was added to the reaction mixture and insoluble materials were filtered out. The filtrate was washed with dilute HCl-ice water and saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residues was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (40:1) mixture] to obtain 4.17 g of the desired compound (E/Z=ca. 1/1).

1. stirringThe reaction solution was stirred at -60° C. for 1 hour and at room temperature for 12 hours
2. filtrationwere filtered out
3. washThe filtrate was washed with dilute HCl-ice water and saturated sodium chloride solution successively
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was removed under reduced pressure

ORD record

ord-616a03c859f64765998833ccf157e3ba

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04840971