反应详情

A solution of tetrabutylammonium fluoride (1 M) in THF was added dropwise to a solution of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-prop-2-ynyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.49 g) at 0° C. The reaction mixture was allowed to warm up to room temperature, further stirred for 1 h 20 and then, poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 2.47 g of crude mixture were isolated as a yellow oil. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give 0.646 g of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide as a white solid (m.p.=150-150° C.).

1. customThe two layers were separated
2. extractionthe aqueous layer was extracted thrice with ethyl acetate
3. washwashed once with brine
4. dry with materialdried over sodium sulphate
5. filtrationAfter filtration and concentration under reduced pressure 2.47 g of crude mixture
6. customwere isolated as a yellow oil
7. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate)