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

HRID 1484128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484128
[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

Komponenten

3

Edukt 2

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6944c73168b84165a979b640f5ef3d8b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09421210B2

Notizen zur Reaktion

Wird geladen…