反应详情

To sodium hydride (0.42 g of a 60% oil dispersion, 0.0105 mol), freed from oil, stirred in dry dimethyl formamide (15 ml) under nitrogen was added methyl 4-(3-methyl-1-oxobutyl)-1H-pyrrole-3-carboxylate (2.2 g) prepared as described in b) above in portions over 20 minutes. After 10 minutes, potassium iodide (0.01 g) and (1-naphthalenyl)methyl chloride (1.85 g) in dimethyl formamide (20 ml) were added. The mixture was stirred for 4 hours and then poured into 0.5M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed well with water and then brine, dried and evaporated to a gum, which was chromatographed with ethyl acetate-isohexane (1:3) to give an oil. The oil was crystallised from cyclohexane to yield the subtitle pyrrole (2.6 g).

1. customprepared
2. customover 20 minutes
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed well with water
5. dry with materialbrine, dried
6. customevaporated to a gum, which
7. customwas chromatographed with ethyl acetate-isohexane (1:3)
8. customto give an oil
9. customThe oil was crystallised from cyclohexane