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

HRID 853801
Notes
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Reaction equation

HRID 853801 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 694715505-Benzyloxy-2-(4-benzyloxyphenyl)isoindoline-1,3-dioneHCID 178418443HCID 178418443, compound

Product 1

HCID 694720885-Benzyloxy-2-(4-benzyloxyphenyl)-3-ethyl-3-hydroxyisoindolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureto warm to room temperature for 2 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes