Dimethyl Sulfoxide → 2-Methyl-5-(2-methyloxiran-2-yl)pyridine

HRID 1400364

Reaktionsgleichung

Reaktionsgleichung von HRID 1400364
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[CH3:12][C:13]1[N:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1>C1COCC1>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([CH3:8])[CH2:20][O:21]2)=[CH:17][N:18]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 952923-Acetyl-6-methylpyridine

Produkt 1

HCID 594552552-Methyl-5-(2-methyloxiran-2-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents stirred for 10 min. after which the solution of 1-(6-methylpyridin-3-yl)ethanone (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

Aufarbeitung

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Quellen und Nachweise

ORD-Eintrag
ord-6b52658adc9f4ce2b0cba25d94af68f6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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