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

HRID 19524

Reaction equation

[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].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([Mg]Br)[CH:29]=[CH:30][CH:31]=1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([O:25][CH3:24])[CH:31]=2)[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]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (100 mg, 0.325 mmol) obtained in Example 1 was dissolved in THF and 1.5 equivalents of 3-methoxyphenylmagnesium bromide were added thereto, followed by stirring for 1 hr at 0° C. Then, the reaction 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 122 mg of the titled compound (yield: 90.4%).

Workup

washThen, the reaction 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

Sources & evidence

ORD record: ord-561fdd55bd744beb8d9bda76c4e9af68
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745439B2

Linked notes

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