3-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde → HCID 68938969, compound

HRID 242719Notes

Reaction equation

HRID 242719 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:32]=[C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](=[O:42])[N:34]1[CH2:43][CH2:44][CH2:45][C:46]1[CH:47]=[C:48]([CH:51]=[CH:52][CH:53]=1)[CH:49]=O>>[CH3:31][O:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:4]([O:3][CH3:2])[C:5]=1/[CH:6]=[CH:49]/[C:48]1[CH:47]=[C:46]([CH2:45][CH2:44][CH2:43][N:34]2[C:35](=[O:42])[C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:33]2=[O:32])[CH:53]=[CH:52][CH:51]=1

Participants

3

Reactant 2

HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehydeHCID 86632153HCID 86632153, compound

Product 1

HCID 68938969HCID 68938969, compound

Procedure

2,6-Dimethoxybenzyltriphenylphosphonium bromide was coupled with phthalimide 29 following the method used in Example 44, except that the reaction was stirred overnight after warming up to room temperature. After concentration under reduced pressure, the residue was partitioned between EtOAc and water. The combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (7 to 60% EtOAc-hexanes gradient) gave (E)-2-(3-(3-(2,6-dimethoxystyryl)phenyl)propyl)isoindoline-1,3-dione as a light yellow oil. Yield (0.317 g, 82%): 1H NMR (400 MHz, DMSO-d6) δ 7.79-7.84 (m, 4H), 7.42 (d, J=17.2 Hz, 1H), 7.17-7.32 (m, 5H), 7.06-7.09 (m, 1H), 6.58 (d, J=8.4 Hz, 2H), 3.83 (s, 6H), 3.61 (t, J=7.2 Hz, 2H), 2.63 (t, J=8.0 Hz, 2H), 1.88-1.96 (m, 2H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (7 to 60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-5c03eb02768441d180ac729a9a5f2258
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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