反应详情

Sodium (2.3 g; 0.10 mol) was allowed to react with dry ethanol (50 ml) under nitrogen. The resulting clear solution was cooled (ice bath) and t-butyl acetoacetate (15.8 g; 0.10 mol) was added during 10 minutes with stirring. After 10 minutes, 2-(bromoethyl)benzene (18.5 g; 0.10 mol) was added during 30 minutes. The resulting solution was heated at reflux for 4 hours, then cooled and filtered. After concentration, the residue was partitioned between water and ether, and the ether layer was dried (MgSO4) and concentrated. Distillation of the residue gave 21.0 g (0.080 mol; 80%) of the title product; bp 110°-120° (0.3 mm). NMR (CDCL3); 1.45 (9H,s), 2.17 (3H,s), 1.8-2.4 (2H,m), 2.5-2.7 (2H,m); 3.28 (1H,J=7); 7.2-7.4 (5H, broad s). MS (m/e); 262 (M+).

1. additionwas added during 10 minutes
2. temperatureThe resulting solution was heated
3. temperatureat reflux for 4 hours
4. temperaturecooled
5. filtrationfiltered
6. concentrationAfter concentration
7. customthe residue was partitioned between water and ether
8. dry with materialthe ether layer was dried (MgSO4)
9. concentrationconcentrated
10. distillationDistillation of the residue