反应详情

Ethyl 2-carboethoxy-4[4'-(4"-chlorophenyl) phenyl]-4-oxobutanoate (0.40 g, 1.02 mmol) was added in one portion at rt to a solution of sodium ethoxide (0.08 g, 1.12 mmol) in DME (1 mL). After 15 min, 4-phenyl-1-iodobutane (0.24 g, 0.93 mmol) in DME (3 mL) was added. The resulting solution was stirred for 18 h. The solvent was concentrated in vacuo and the resulting oil dissolved in CH2Cl2 (100 mL) and washed with water (100 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic phases were dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel using a gradient of ethyl acetate/hexane (10% to 25% ethyl acetate) as the eluent to afford a crystalline solid which was recrystallized with hexane and ethyl acetate to afford 1-[4'-(4"-chlorophenyl)phenyl]-3,3-dicarboethoxy-1-oxo-7-phenylheptane (0.272 g, 28%).

1. concentrationThe solvent was concentrated in vacuo
2. dissolutionthe resulting oil dissolved in CH2Cl2 (100 mL)
3. washwashed with water (100 mL)
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with CH2Cl2 (2×50 mL)
6. dry with materialThe combined organic phases were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting oil was purified by flash chromatography on silica gel using a gradient of ethyl acetate/hexane (10% to 25% ethyl acetate) as the eluent
10. customto afford a crystalline solid which
11. customwas recrystallized with hexane and ethyl acetate