2-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

HRID 2383370Notes

Reaction equation

HRID 2383370 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:6][CH:5]=1>C(OCC)(=O)C.[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Rh+3].[Cl-].[Cl-]>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

Product 1

HCID 591459612-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dioneYield 85%

Reagents, catalysts & solvents 2

HCID 21948325Rhodium tris(triphenylphosphine)chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-{2-[4-(2-hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione (Preparation 9, 62.0 g, 211.37 mmol) was dissolved in ethyl acetate (1200 mL). To this was added rhodium tris(triphenylphosphine)chloride, (12.7 g, 13.7 mmol) and the mixture hydrogenated at 20 psi, room temperature for 24 hours. The reaction was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate (1000 mL) and passed through a pad of silica gel, washing with ethyl acetate. The solvent was removed in vacuo to yield a light brown solid which was recrystallised from ethyl acetate:heptane (4:1, by volume) to yield the title compound as an off-white crystalline solid, in 85% yield, 53 g,

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (1000 mL)
  4. washwashing with ethyl acetate
  5. customThe solvent was removed in vacuo
  6. customto yield a light brown solid which
  7. customwas recrystallised from ethyl acetate:heptane (4:1, by volume)

Sources & evidence

ORD record
ord-b7e86227c30a42d1873dac977e6ca476
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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