Phthalimide → HCID 57608529, compound

HRID 517110Notes

Reaction equation

HRID 517110 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1[C:39]#[C:40][C:41]1[CH:42]=[C:43]([CH:47](O)[CH2:48][CH3:49])[CH:44]=[CH:45][CH:46]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:33]=1[C:39]#[C:40][C:41]1[CH:42]=[C:43]([CH2:47][CH2:48][CH2:49][N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])[CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66629134HCID 66629134, compound

Product 1

HCID 57608529HCID 57608529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.087 g, 0.33 mmol), phthalimide (0.0.49 g, 0.33 mmol) and (3-((2,6-dimethylphenyl)ethynyl)phenyl)propan-1-ol (12) (0.085 g, 0.32 mmol) were dissolved in anhydrous THF (3 mL) under argon, and the solution was cooled over an ice bath. Diethyl azodicarboxylate (0.052 mL, 0.33 mmol) was added dropwise with rapid stirring, and the resulting mixture was stirred at room temperature for 2.5 h. The reaction mixture was concentrated under reduced pressure and purified by flash chromatography (6 to 60% EtOAc-hexanes gradient) to yield 2-(3-(3-((2,6-dimethylphenyl)ethynyl)phenyl)propyl)isoindoline-1,3-dione (13) as a white solid. Yield (0.095 g, 75%): 1H NMR (400 MHz, DMSO-d6) δ 7.82-7.89 (m, 4H), 7.42 (s, 1H), 7.13-7.35 (m, 6H), 3.63 (t, J=7.2 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 2.51 (s, 6H), 1.90-1.97 (m, 2H).

Workup

  1. temperaturethe solution was cooled over an ice bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by flash chromatography (6 to 60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-8798be9be44e4fd38f3af8621a39eb09
Source dataset
uspto-grants-2015_08
Patent number
US09115056B2

Reaction notes

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