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

HRID 242726노트

반응식

HRID 242726 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7812c15a44cf4705933650ab14a2e9db
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653142B2

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