Ethanol → Fenoprofen

HRID 1277761

Reaktionsgleichung

Reaktionsgleichung von HRID 1277761
CS[C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH3:7])[C:4]([OH:6])=[O:5].[Na].C(O)C>C(O)(C)(C)C.O1CCCC1>[O:14]([C:10]1[CH:9]=[C:8]([CH:3]([CH3:7])[C:4]([OH:6])=[O:5])[CH:13]=[CH:12][CH:11]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 5360545SodiumHCID 12917672alpha-Methylthio-alpha-(m-phenoxyphenyl)propionic acid

Produkt 1

HCID 3342FenoprofenAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

α-Methylthio-α-(m-phenoxyphenyl)propionic acid (288 mg) was dissolved in a mixture of 1 ml of t-butanol and 4 ml of tetrahydrofuran, and 100 mg of metallic sodium was added. The mixture was stirred at room temperature for 10 minutes. The mixture was heated under reflux for an additional 1.5 hours with stirring. After cooling, a small amount of ethanol was added to consume the unreacted metallic sodium completely. Water (20 ml) was added, and the pH of the mixture was adjusted to 1 with conc. hydrochloric acid. The mixture was extracted three times with 27 ml of diethyl ether. The extract was washed twice with 20 ml of water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and chromatographed on a silica gel column using methylene chloride as an eluent to afford 234 mg of α-(m-phenoxyphenyl)propionic acid in a yield of 97%.

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for an additional 1.5 hours
  4. stirringwith stirring
  5. temperatureAfter cooling
  6. customto consume the unreacted metallic sodium completely
  7. additionWater (20 ml) was added
  8. extractionThe mixture was extracted three times with 27 ml of diethyl ether
  9. washThe extract was washed twice with 20 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customchromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-0da7657d2b4043b2b7734a3314e7d90a
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04278802

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