Dimethyl Sulfoxide → 2-(2,4-Dichlorophenyl)-2-methyloxirane

HRID 1045538

Reaktionsgleichung

Reaktionsgleichung von HRID 1045538
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:22])[CH3:21]>C1COCC1>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20]1([CH3:8])[CH2:21][O:22]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 166932',4'-DichloroacetophenoneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Produkt 1

HCID 199924372-(2,4-Dichlorophenyl)-2-methyloxirane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The title compound was prepared by following general procedure 3. DMSO was added to NaH (1 equiv.) and heated to 65° C. for 1 h. THF was added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1 equiv.) was added and the reaction mixture was stirred for 10 min. after which the solution of 1-(2,4-dichlorophenyl)ethanone (1 equiv.) in THF was added dropwise. After complete addition, the reaction mixture was stirred at RT for 2 h. The product was detected by LCMS and the reaction mixture was poured into ice water, extracted in diethyl ether (4×50 mL), dried over Na2SO4 and concentrated at 25° C. to obtain the product.

Aufarbeitung

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture was cooled to 0° C
  3. additionwas added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether (4×50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at 25° C.
  8. customto obtain the product

Quellen und Nachweise

ORD-Eintrag
ord-501f254d3b3940dc8387e8bc9a45963f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569287B2

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