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Ethylene Oxide → 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-one

HRID 626074
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626074
[CH2:1]([O:8][C:9](=[O:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][C:19]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:13]([F:34])[CH:12]=1)[C:2]1C=CC=CC=1.C([Li])CCC.C1OC1>O1CCCC1>[CH2:27]([O:26][C:19]1[CH:20]=[C:21]([CH2:24][CH3:25])[CH:22]=[CH:23][C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[CH2:2][CH2:1][O:8][C:9]2=[O:35])=[CH:12][C:13]=1[F:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6354Ethylene OxideHCID 59191307[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 178418339Butyllithium

Produkt 1

HCID 591913503-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of [4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-carbamic acid-benzyl ester (500 mg, 1.06 mmol) in 5 ml tetrahydrofuran under nitrogen atmosphere was cooled to −78° C. To this added 2.8M n-butyl lithium (0.075 g, 1.16 mmol) dropwise and the stirring at −78° C. for 1 h. Condensed ethylene oxide (0.5 ml, 9.9 mmol) was then added dropwise to the reaction mixture and warmed slowly to rt. The reaction was stirred at rt overnight and then quenched with saturated ammonium chloride solution. The aqueous phase was extracted with dichloromethane and the combined organic phase was dried over anhydrous Na2SO4 and concentrated. The crude obtained was purified by column chromatography on silica gel using 25% ethyl acetate in petroleum ether as eluant to obtain 350 mg, 81% of the title compound as a brown oil.

Aufarbeitung

  1. additionwas then added dropwise to the reaction mixture
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude obtained
  7. customwas purified by column chromatography on silica gel using 25% ethyl acetate in petroleum ether as eluant

Quellen und Nachweise

ORD-Eintrag
ord-63047eb77570487d9b20c741405a97c5
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309179B2

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