反应详情

A solution of isopropyltriphenylphosphonium bromide (326 mg; 0.75 mmol) in 1.5 ml of dry THF was treated in an ice bath, under nitrogen, with n-butyl lithium (0.425 ml of a 1.6M solution in hexane; 0.68 mmol), dropwise. After stirring for 15 minutes, this mixture was added, via syringe, into an ice-cold solution of ethyl 2-[4-(2-{(5-formylpyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (200 mg; 0.38 mmol) in 2 ml of dry THF. After stirring at rt overnight, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (5–20% gradient) afforded ethyl 2-methyl-2-[4-(2-{[5-(2-methylprop-1-enyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]propanoate (70 mg; 33% yield).

1. stirringAfter stirring at rt overnight
2. customthe reaction mixture was partitioned between ethyl acetate and water
3. washThe organic phase was washed with water and brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification by radial chromatography