反应详情

Sodium (1.0 g, 43 mmol) was dissolved in MeOH (50 mL) and then evaporated to a dry white powder. To the powder was added MTBE (100 mL) and diethyloxalate (5.14 g, 35.2 mmol). To the resulting solution was added a solution of 1-(4-methylphenyl)ethanone (5.0 g, 37.3 mmol) in MTBE (50 mL) dropwise over 45 min. The resulting suspension was allowed to stir for 1 h, and the precipitate was filtered and washed with MTBE/hexanes (1:1, 50 mL). The solid was suspended in 1 N HCl (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were dried (MgSO4), filtered, and concentrated to an oily residue which crystallized on standing at rt. The yellow solid was triturated with MTBE/hexanes (1:1) and filtered to give the title compound (3.76 g, 46%) as a white solid.

1. customevaporated to a dry white powder
2. filtrationthe precipitate was filtered
3. washwashed with MTBE/hexanes (1:1, 50 mL)
4. extractionextracted with EtOAc (2×100 mL)
5. dry with materialThe combined extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated to an oily residue which
8. customcrystallized
9. customon standing at rt
10. customThe yellow solid was triturated with MTBE/hexanes (1:1)
11. filtrationfiltered