Dimethyl Sulfoxide → 2-(3-Fluoro-4-methoxyphenyl)oxirane

HRID 1400354

Reaktionsgleichung

Reaktionsgleichung von HRID 1400354
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=[O:17]>C1COCC1>[F:12][C:13]1[CH:14]=[C:15]([CH:16]2[CH2:8][O:17]2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 676963-Fluoro-p-anisaldehydeHCID 75127Trimethylsulfonium iodide

Produkt 1

HCID 246990792-(3-Fluoro-4-methoxyphenyl)oxirane

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 3-fluoro-4-methoxybenzaldehyde (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. The reaction mixture is poured in ice water, extracted in diethyl ether (4×50 mL), 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 (4×50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Quellen und Nachweise

ORD-Eintrag
ord-8958b571ee4f40609b3b0d258516795f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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