反应详情

To a solution of diisopropylamine (17 ml) in THF (tetrahydrofuran) (210 ml) was added n-butyllithium (67 ml, 1.6N in hexane) at -78° C. under N2. The solution was stirred for 30 minutes at 0° C. and then cooled to -78° C. To the solution was added ethyl acetate (12 g) and the mixture was stirred for 30 minutes at the same temperature to give Li-enolate solution. A solution of 5-t-butyldiphenylsilyloxy-1-oxo-1,2,3,4-tetrahydronaphthalene (10 g) in THF (50 ml) was cooled to -78° C., the above Li-enolate solution (35 ml) was added, and stirred for 1 hour at the same temperature. The mixture was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N--HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-hydroxy-1-ethoxycarbonylmethyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (8.0 g). 2.72 (2H, t, J=6.6 Hz), 2.90 (2H, t, J=8.0 Hz), 4.30 (2H, t, J=7.0 Hz), 5.78 (1H, t, J=4.4 Hz), 6.33 (1H d, J=8 Hz), 6.6-6.9 (2H, m), 7.1-7.8 (20H, m) MS m/z: 624 (M+ +1)

1. washThe organic layer was washed with 1N
2. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
3. customevaporated in vacuo
4. customThe residue was purified by chromatography on silica gel