反应详情

温度

0 °C

Methylacetoacetate (1.63 mL, 15.1 mmol) was dissolved in dry THF (42 mL) and cooled to 0° C. NaH (60% in mineral oil, 0.604 g, 15.1 mmol) were carefully added and the reaction mixture was stirred for 20 min. A solution of BuLi in hexanes (1.6 M, 9.44 mL, 15.1 mmol) was added dropwise and the resulting mixture was stirred an additional 20 min. A solution of 3-(4-benzyloxyphenyl)-1-cyclopentylpropan-1-one (2.33 g, 7.55 mmol) from Step 5 above in THF (37 mL) was added dropwise. After stirring 1 h, the reaction mixture was quenched with saturated aq NH4Cl (100 mL) and extracted with Et2O (600 mL). The organic phase was dried over MgSO4 and evaporated. The residue was then stirred overnight in a mixture of 0.1 M NaOH (370 mL) and THF (37 mL). After the addition of an aq solution of 10% aq KHSO4 (50 mL) the resulting mixture was stirred 30 min and then extracted with Et2O (600 mL). The organic phase was washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography (50% EtOAc in hexanes) to give the product (1.54 g, 52%) as a white foam.

1. stirringthe resulting mixture was stirred an additional 20 min
2. stirringAfter stirring 1 h
3. customthe reaction mixture was quenched with saturated aq NH4Cl (100 mL)
4. extractionextracted with Et2O (600 mL)
5. dry with materialThe organic phase was dried over MgSO4
6. customevaporated
7. stirringThe residue was then stirred overnight in a mixture of 0.1 M NaOH (370 mL) and THF (37 mL)
8. additionAfter the addition of an aq solution of 10% aq KHSO4 (50 mL) the resulting mixture
9. stirringwas stirred 30 min
10. extractionextracted with Et2O (600 mL)
11. washThe organic phase was washed with brine
12. dry with materialdried over MgSO4
13. customevaporated
14. customThe residue was purified by flash column chromatography (50% EtOAc in hexanes)