1-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl ester → 1-hydroxy-1,3-diphenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl ester

HRID 19540Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:30])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[C:9]([O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]=2)=[O:4].[C:31]1([Mg]Cl)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:30])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[C:9]([O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH:8]=2)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile (350 mg, 0.878 mmol) obtained in Step 1 was dissolved in THF, and phenylmagnesium chloride (0.483 mL, 0.966 mmol) was added thereto, followed by stirring for 3 hrs at 0° C. Upon the completion of the reaction, the 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 378 mg of the titled compound (yield: 90%).

Workup

customUpon the completion of the reaction
washthe 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-da7fdcea465a4d1482f088d4455d5142
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745439B2

Reaction notes

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