HCID 42917271, compound → HCID 68941017, compound

HRID 1967677Notes

Reaction equation

HRID 1967677 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[Br-].[CH3:24][C:25]1[CH:50]=[C:49]([CH3:51])[CH:48]=[C:47]([CH3:52])[C:26]=1[CH2:27][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:52][C:47]1[CH:48]=[C:49]([CH3:51])[CH:50]=[C:25]([CH3:24])[C:26]=1/[CH:27]=[CH:18]/[C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 42917271HCID 42917271, compoundHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 1

HCID 68941017HCID 68941017, compound

Procedure

Phthalimide 29 was coupled with 2,4,6-trimethylbenzyltriphenylphosphonium bromide to give (E)-2-(3-(3-(2,4,6-trimethylstyryl)phenyl)propyl)isoindoline-1,3-dione. Yield (0.2485 g, 46%), trans-/cis-isomer ratio 4:1. Trans-isomer: 1H NMR (400 MHz, CDCl3) δ 7.84-7.87 (m, 2H), 7.72-7.74 (m, 2H), 7.26-7.36 (m, 3H), 7.16 (s, 1H), 7.12 (d, J=16.4 Hz, 1H), 6.94 (s, 2H), 6.57 (d, J=16.8 Hz, 1H), 3.82 (t, J=7.2 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.39 (s, 6H), 2.33 (s, 3H), 2.10-2.17 (m, 2H).

Sources & evidence

ORD record
ord-da700d8d31484a04aa6252cef1702ff2
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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