Potassium Carbonate → Diethyl 4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-dicarboxylate

HRID 336320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336320
CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:20])([S:17][S:18][CH3:19])[CH3:16])(=O)=O)=CC=1.O[C:22]1[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:25]=[C:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:20][C:15]([S:17][S:18][CH3:19])([CH3:16])[CH2:14][CH2:13][CH2:12][O:11][C:22]1[CH:23]=[C:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:25]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:27]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 866712794-Methyl-4-(methyldisulfanyl)pentyl 4-methylbenzenesulfonateHCID 178469316HCID 178469316, Verbindung

Produkt 1

HCID 86671278Diethyl 4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-dicarboxylateAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 4-methyl-4-(methyldisulfanyl)pentyl 4-methylbenzenesulfonate (5c) (0.48 g, 1.435 mmol) and diethyl 4-hydroxypyridine-2,6-dicarboxylate (5a)(0.343 g, 1.435 mmol) in anhydrous dimethylformamide (6.5 mL) was added Potassium carbonate (0.297 g, 2.152 mmol). The reaction was stirred at 90° C. for 18 hours. Then allowed to cool to ambient temperature and quenched with saturated ammonium chloride. The mixture was extracted three times with ethyl acetate. The extracts were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (30% hexanes/ethyl acetate) yielded diethyl 4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-dicarboxylate (5d)(300 mg, 52%); 1H NMR (400 Hz, CDCl3): δ 7.70 (s, 2H), 4.40 (q, 4H, J=7.2, 14.4 Hz), 4.07 (t, 2H, J=6. Hz), 2.35 (s, 3H), 1.86 (m, 2H), 1.70 (m, 2H), 1.38 (t, 6H, J=7.2 Hz), 1.27 (s, 6H); MS (m/z). found 424.1 (M+Na), 440.1 (M+K). See FIG. 5.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customquenched with saturated ammonium chloride
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. dry with materialThe extracts were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (30% hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-044c8db726244bbba46161e39581dc8c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889669B2

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