Ethyl benzoylformate → Ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate

HRID 1289811

Reaktionsgleichung

Reaktionsgleichung von HRID 1289811
[CH:1]1([Mg]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH:1]1([C:14]([OH:20])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 15349Ethyl benzoylformateHCID 25517Ammonium ChlorideHCID 178478989HCID 178478989, Verbindung

Produkt 1

HCID 12322152Ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of cyclopentylmagnesium chloride in diethyl ether was added dropwise to a solution of 23.5 g of ethyl phenylglyoxylate in 200 ml of tetrahydrofuran under cooling with ice, and this mixture was stirred at the same temperature for 30 minutes. After the addition of a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 20/1) to obtain 11 g of ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate. This was dissolved in 40 ml of methanol, and 20 ml of a 4N aqueous solution of sodium hydroxide was added thereto at room temperature. This mixture was stirred at the same temperature for 2 hours and then at 50° C. for an hour. After the methanol was distilled off under reduced pressure, the aqueous layer was made weakly acidic with 4N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting solid was washed with diethyl ether/hexane (=1/1) to obtain 8.7 g of the title compound.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-47679b31e56e4b5bb35bf0d64560fb1c
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750540

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