(2-Hydroxybenzyl)triphenylphosphonium bromide → (E)-2-(3-(3-(2-hydroxystyryl)phenyl)propyl)isoindoline-1,3-dione

HRID 242726Notes

Reaction equation

HRID 242726 reaction equation
[Br-].[OH:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:29]=[C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[N:31]1[CH2:40][CH2:41][CH2:42][C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][CH:50]=1)[CH:46]=O>>[OH:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1/[CH:5]=[CH:46]/[C:45]1[CH:44]=[C:43]([CH2:42][CH2:41][CH2:40][N:31]2[C:32](=[O:39])[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:30]2=[O:29])[CH:50]=[CH:49][CH:48]=1

Participants

3

Reactant 2

HCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 1

HCID 68937230(E)-2-(3-(3-(2-hydroxystyryl)phenyl)propyl)isoindoline-1,3-dione

Procedure

2-Hydroxybenzyltriphenylphosphonium bromide was coupled with phthalimide 29 according to the method used in Example 45 except that the reaction was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure and partitioned between EtOAc and water. The combined organics were washed with saturated aqueous NH4Cl and water, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (5 to 60% EtOAc-hexanes gradient) gave (E)-2-(3-(3-(2-hydroxystyryl)phenyl)propyl)isoindoline-1,3-dione as a light yellow foam. Yield (0.165 g, 43%): 1H NMR (400 MHz, DMSO-d6) δ 9.69 (s, 1H), 7.78-7.84 (m, 4H), 7.53 (dd, J=8.0, 1.6 Hz, 1H), 7.28-7.38 (m, 3H), 7.22 (t, J=8.4 Hz, 1H), 7.05-7.14 (m, 3H), 6.76-6.86 (m, 2H), 3.61 (t, J=6.8 Hz, 2H), 2.63 (t, J=7.2 Hz, 2H), 1.89-1.97 (m, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. custompartitioned between EtOAc and water
  3. washThe combined organics were washed with saturated aqueous NH4Cl and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (5 to 60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-7812c15a44cf4705933650ab14a2e9db
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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