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