Methanesulfonic Acid → 5-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl ester

HRID 17893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17893
[CH2:1]([O:3][C:4](=[O:22])[C:5]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1)=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:5]1[C:13](=[O:21])[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:22])[CH3:2]

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 686968932-(3-Methylbenzoyl)-3-phenyl acrylic acid ethyl ester

Produkt 1

HCID 686992925-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl esterAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(3-Methylbenzoyl)-3-phenylacrylate ethyl ester (1 g, 3.39 mmol) was dissolved in dichloromethane. Methanesulfonic acid (5.22 g, 54.35 mmol) was added thereto and the mixture was stirred for 3 hours at room temperature. After the reaction was completed, the mixture was cooled to 0° C. followed by neutralizing with sodium bicarbonate. Then, the separated organic layer extracted with dichloromethane was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9) to obtain 5-methyl-3-oxo-1-phenyl-indene-2-carboxylate ethyl ester (273 mg, yield 27%).

Aufarbeitung

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionThen, the separated organic layer extracted with dichloromethane
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-fada14fd79874a08aa476e6d2f4438cf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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