Reaktion #965732

Reaktionsgleichung

1-(4-methylphenyl)ethanone

Sodium

diethyloxalate

→

title compound

Ausbeute 48.5%

methyl 4-(4-methylphenyl)-2,4-dioxobutanoate

Ausbeute 48.5%

Lösungsmittel

MTBE

MeOH

MTBE

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated to a dry white powder
2. 2
   Filtrationthe precipitate was filtered
3. 3
   Waschenwashed with MTBE/hexanes (1:1, 50 mL)
4. 4
   Extraktionextracted with EtOAc (2×100 mL)
5. 5
   TrocknenThe combined extracts were dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to an oily residue which
8. 8
   Sonstigecrystallized
9. 9
   Sonstigeon standing at rt
10. 10
    SonstigeThe yellow solid was triturated with MTBE/hexanes (1:1)
11. 11
    Filtrationfiltered

Vorschrift

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.

Quelle