Potassium Carbonate → Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate

HRID 1443264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443264
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10](O)([CH3:12])[CH3:11].[CH2:14]([O:16][C:17](=[O:25])[C:18]([O:20][Si](C)(C)C)=[CH2:19])[CH3:15].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:14]([O:16][C:17](=[O:25])[C:18](=[O:19])[CH2:20][C:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])([CH3:12])[CH3:11])[CH3:15]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 179891622-(2-Methoxy-3-methylphenyl)propan-2-ol

Produkt 1

HCID 17989129Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoateAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

71.37 g (395.96 mmol) of 2-(2-methoxy-3-methylphenyl)-propan-2-ol and 149 g (791.92 mmol) of 2-trimethylsilanyloxyacrylic acid ethyl ester are introduced into 1.1 l of dichloromethane. At −78° C., 44.8 ml (379.91 mmol) of tin tetrachloride is added in drops, and the batch is then stirred for three hours at this low temperature. 1.4 l of semiconcentrated potassium carbonate solution is added in drops, and the reaction mixture is thus brought to room temperature. The batch is filtered, and the filtrate is extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried on sodium sulfate, and the solvent is spun off. The residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane). The residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane). 45.81 g (41.6%) of the desired compound is isolated.

Aufarbeitung

  1. customis thus brought to room temperature
  2. filtrationThe batch is filtered
  3. extractionthe filtrate is extracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. customdried on sodium sulfate
  6. customThe residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane)
  7. customThe residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-10549c8c5312464e8e82fd08779747ef
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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