Ammonium Chloride → 5-Benzyloxy-2-(4-benzyloxyphenyl)-3-ethyl-3-hydroxyisoindolin-1-one

HRID 853801Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=1)[C:12]2=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]([Mg]Br)[CH3:35].[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][CH:20]=1)[C:12]2([CH2:34][CH3:35])[OH:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 3 °C

Procedure

To a cooled (3° C.) solution containing 5-benzyloxy-2-(4-benzyloxyphenyl)-isoindoline-1,3-dione (870 mg) in THF (25 mL) under nitrogen atmosphere was added ethylmagnesium bromide (4 mL, 3M solution in THF) dropwise. The mixture was stirred at 3° C. for 15 min then allowed to warm to room temperature for 2 h. The mixture was cooled, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine. Evaporation of the solvent yielded the title compound (900 mg) as a tan solid. MS: 466 (MH+).

Workup

temperatureto warm to room temperature for 2 h
temperatureThe mixture was cooled
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
customEvaporation of the solvent

Sources & evidence

ORD record: ord-694bf047133046ddb5461eb3110a395e
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256201B2

Reaction notes

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