Potassium Carbonate → Nabumetone

HRID 1457421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457421
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[CH:14][C:15](=[O:17])[CH3:16])[CH:7]=[CH:6]2.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Pd]>[CH3:16][C:15]([CH2:14][CH2:13][C:8]1[CH:7]=[CH:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[CH:9]=1)=[O:17]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 534099264-(6-Methoxy-2-naphthalenyl)-3-buten-2-one

Produkt 1

HCID 4409NabumetoneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(6-Methoxy-2-naphthyl)-but-3-en-2-one (100.0 g, 0.442 mol), (6.0 g), and potassium carbonate (13 g) were slurried in ethyl acetate (1100 mL), stirred 15 minutes, and 5% Pd/C (9.0 g) was added. The flask was purged with H2, a H2 balloon was added, and the reaction was followed by GC. After 12.5 hours, the reaction mass was filtered, washed with H2O (2×150 mL), dried (Na2SO4), filtered, and concentrated in vacuo, affording 95.3 g (95%) of nabumetone (93% purity, 98.5:1.5 ketone:alcohol ratio). The product was recrystallized from EtOH (275 mL) to give 81 g (80%) of 99% nabumetone (92% recovery of contained product). mp 79.5° C.; DSC 81.8° C.; 1H NMR (300 MHz, CDCl3) δ 7.61 (d,2H), 7.48 (s,1H), 7.22 (dd,1H), 7.12-7.04 (m,2H); 13C NMR (75 MHz, CDCl3) δ 208.2, 157.8, 136.6, 133.6, 129.6, 129.4, 128.0, 127.4, 126.7, 119.3, 106.2, 55.7, 45.5, 30.5, 30.2.

Aufarbeitung

  1. customThe flask was purged with H2
  2. additiona H2 balloon was added
  3. waitAfter 12.5 hours
  4. filtrationthe reaction mass was filtered
  5. washwashed with H2O (2×150 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-362bb9ac3e664b0f800f93d93eececc1
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05847225

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