6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester → 1-hydroxy-6-(2-morpholine-4-yl-ethoxy)-1,3-diphenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19532Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:30])[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][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH:9]=2)=[O:5])[CH3:2].[C:31]1([Mg]Cl)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:30])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)[CH:9]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

6-(2-Morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1.5 g, 3.68 mmol) obtained in Step 1 was dissolved in THF, and phenylmagnesium chloride (3.865 mL, 5.89 mmol) was added thereto, followed by stirring for 2 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 788 mg of the titled compound (yield: 44%).

Workup

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

Sources & evidence

ORD record: ord-a6480cd15f0049b7956b96c9ea167dc3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745439B2

Reaction notes

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