反应详情

A solution of diethyl 2-phenyl-2-(2-methyl-2-propenyl)malonate (1.63 g, 5.6 mmole) in 20 mL of EtOH and 5 mL of H2O was treated with NaOH (2 g), and refluxed for 3 hours. The reaction was cooled, diluted with H2O, and washed with Et2O. The aqueous layer was acidified and extracted with CH2Cl2. The extracts were dried and evaporated. The residue was dissolved in 5 mL of dimethylacetamide and heated to 125° for 1 hour. The reaction was cooled, diluted with H2O, acified, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent removed. The residue was dissolved in 10 mL of MEOH, a drop of concentrated H2SO4 was added, and stirred for 24 hours. The reaction was diluted with H2O, and extracted with Et2O. The extracts were washed with H2O, aqueous NaHCO3, dried and the solvent removed, and gave the titled compound, 953 mg (83%). MS (ESI) 205 (MH+)

1. temperaturerefluxed for 3 hours
2. temperatureThe reaction was cooled
3. washwashed with Et2O
4. extractionextracted with CH2Cl2
5. customThe extracts were dried
6. customevaporated
7. dissolutionThe residue was dissolved in 5 mL of dimethylacetamide
8. temperatureheated to 125° for 1 hour
9. temperatureThe reaction was cooled
10. additiondiluted with H2O
11. extractionextracted with Et2O
12. washThe extracts were washed with H2O
13. customdried
14. customthe solvent removed
15. dissolutionThe residue was dissolved in 10 mL of MEOH
16. additiona drop of concentrated H2SO4 was added
17. additionThe reaction was diluted with H2O
18. extractionextracted with Et2O
19. washThe extracts were washed with H2O, aqueous NaHCO3
20. customdried
21. customthe solvent removed