反应详情

2-naphthylacetonitrile (3.45 g, 20.6 mmol) and methyl acrylate (9.7 ml, 107 mmol) were suspended in 2-methyl-2-propanol (10 ml). Heat was applied to the reaction vessel until the solution became clear. The mixture was cooled to room temperature, at which time (Bu)4NOH (6.9 mmol, 0.33 equiv.) was added as a solution in 2-methyl-2-propanol:methanol (1:2). The combined reaction mixture was heated to reflux for 4 h under vigorous stirring at which time the reaction appeared complete by GC-MS. After allowing the reaction to cool the mixture was partitioned between H2O (75 ml) and EtOAc (50 ml). The aqueous layer was removed and washed with EtOAc (2×50 ml). The combined organic phases were washed with NaHCO3 (sat. aq.) and brine and dried over MgSO4. After filtration the solvent was removed in vacuo. The crude product was purified by flash column chromatography (25% EtOAc in hexanes) to isolate the title compound as a light yellow oil (5.75 g, 82%).

1. temperatureHeat
2. customThe combined reaction mixture
3. temperaturewas heated
4. temperatureto reflux for 4 h
5. customthe reaction
6. temperatureto cool the mixture
7. customwas partitioned between H2O (75 ml) and EtOAc (50 ml)
8. customThe aqueous layer was removed
9. washwashed with EtOAc (2×50 ml)
10. washThe combined organic phases were washed with NaHCO3 (sat. aq.) and brine
11. dry with materialdried over MgSO4
12. filtrationAfter filtration the solvent
13. customwas removed in vacuo
14. customThe crude product was purified by flash column chromatography (25% EtOAc in hexanes)