p-Toluenesulfonic acid → 1-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl ester

HRID 17896

Reaktionsgleichung

Reaktionsgleichung von HRID 17896
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:31])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:3][C:4]([C:6]1[C:7](=[O:31])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:9]=2)=[O:5]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 118452821-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

Produkt 1

HCID 687010351-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl esterAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate ethyl ester (1.65 g, 4.0 mmol) prepared in (Step 5) of Example 1 was dissolved in methanol (160 ml) and p-toluene sulfonic acid (228 mg, 1.2 mmol) was added thereto. The mixture was reacted for 1 hour at 70° C., and then washed with brine. The organic layer was extracted with ethyl acetate, dried over anhydrous sulfonate sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain the title compound (yield 75.3%) as a red solid.

Aufarbeitung

  1. customThe mixture was reacted for 1 hour at 70° C.
  2. washwashed with brine
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sulfonate sulfate
  5. concentrationconcentrated
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Quellen und Nachweise

ORD-Eintrag
ord-3b200dad4b06471d9b74686d147c1eb5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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