Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylate → 1-cyclohexyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19528

Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[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][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH:24]1([Mg]Cl)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)([OH:23])[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][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (78 mg, 0.253 mmol) obtained in Example 1 was dissolved in THF, and 18%-cyclohexylmagnesium chloride (0.7 mL, 0.506 mmol) was added thereto, followed by stirring for 5 hrs at 0° C. The resulting mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 30 mg of the titled compound (yield: 30%).

Aufarbeitung

washThe resulting mixture washed with saturated saline
extractionextracted with ethyl acetate
customThe organic layer was separated
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under a reduced pressure
customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-7a10624842704a7abc2067372af0646d
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745439B2

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