Diethyl Oxalate → Methyl 4-(4-methylphenyl)-2,4-dioxobutanoate

HRID 878550

Reaktionsgleichung

Reaktionsgleichung von HRID 878550
[Na].C(O[C:5](=[O:11])[C:6]([O:8][CH2:9]C)=[O:7])C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1>CO.CC(OC)(C)C>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH2:20][C:5](=[O:11])[C:6]([O:8][CH3:9])=[O:7])=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 7268Diethyl OxalateHCID 8500p-METHYLACETOPHENONEHCID 5360545Sodium

Produkt 1

HCID 308119Methyl 4-(4-methylphenyl)-2,4-dioxobutanoateAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ea916c09d6f94aebbef9b14e61b9f23b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987461B2

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