Sulfuric Acid → 4-[(3,5-dimethylphenyl)-thio]-5-(hydroxymethyl)-6-methyl-2(1H)-pyridinone

HRID 1241536

Reaktionsgleichung

Reaktionsgleichung von HRID 1241536
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:11]([C:18](OCC)=[O:19])=[C:12]([CH3:17])[NH:13][C:14](=[O:16])[CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:11]([CH2:18][OH:19])=[C:12]([CH3:17])[NH:13][C:14](=[O:16])[CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 21935307Ethyl 4-[(3,5-dimethylphenyl)-thio]-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate

Produkt 1

HCID 219352934-[(3,5-dimethylphenyl)-thio]-5-(hydroxymethyl)-6-methyl-2(1H)-pyridinoneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, the intermediate 14 (500 mg; 1.6 mmol) was suspended in dry tetrahydrofurane (20 ml) and LiAlH4 (120 mg; 3.2 mmol) was added at 0° C. The mixture was stirred at room temperature for 18 hours and poured in ethyl acetate (50 ml) at 0° C. and a solution 10% H2SO4 (100 ml) was added dropwise. The mixture was extracted with ethyl acetate (2×100 ml) and the organic layer was removed under reduced pressure giving the intermediate 15 (310 mg; 71%) m.p.=268–270° C.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate (2×100 ml)
  2. customthe organic layer was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-277c288623c843d69a0a9edca89a338b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115608B2

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