反应详情

温度

0 °C

To a suspension of NaH (60%) (815 mg, 20.39 mmol) in THF-HMPA (20 ml, 5 ml) was added methylacetoacetate (2.0 g, 18.5 mmol) in THF (5 ml) at 0° C. The mixture was stirred for 10 min. at 0° C. under nitrogen atmosphere. BuLi (12.3 ml, 20.39 mmol) was dropwise added and the red mixture was stirred for 15 min. at 0° C. Then a solution of chlorothioanisole (2.7 ml, 20.39 mmol) in THF (5 ml) was added to the mixture at 0° C. The mixture was stirred for 1 h at -5° C. The mixture was quenched with H2O, then extracted with AcOEt (100 ml×2). AcOEt layer was washed with H2O (10 ml×2) and brine (10 ml), then dried over MgSO4 and evaporated. The residue was purified by a silica gel column chromatography (150 g, hexane :AcOEt=6:1) to give a colorless oil (1.0 g, 22.7%).

1. stirringthe red mixture was stirred for 15 min. at 0° C
2. stirringThe mixture was stirred for 1 h at -5° C
3. customThe mixture was quenched with H2O
4. extractionextracted with AcOEt (100 ml×2)
5. washAcOEt layer was washed with H2O (10 ml×2) and brine (10 ml)
6. dry with materialdried over MgSO4
7. customevaporated
8. customThe residue was purified by a silica gel column chromatography (150 g, hexane :AcOEt=6:1)