Diethyl Ether → 2-(3-(3-(Benzyloxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74354

Reaktionsgleichung

Reaktionsgleichung von HRID 74354
CCOCC.[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:10]=[CH:11][CH:12]=1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH2:27]([O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:10]=[CH:11][CH:12]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Produkt 1

HCID 673166422-(3-(3-(Benzyloxy)phenyl)propyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Instead of a Mitsunobu reaction, the ether was formed by alkylation as described. A suspension of phenol 58 (1 g, 3.5 mmol), benzyl bromide (0.3 mL, 3.5 mmol), cesium carbonate (1.158 g, 3.5 mmol) in NMP (3.5 mL) was heated at 70° C. for 24 h. The reaction mixture was quenched by the addition of water, extracted with DCM, washed with water, and dried over anhy. Na2SO4. Filtration and concentration under reduced pressure gave the crude product, which was purified by flash chromatography (hexane-ethyl acetate (0-30%) gradients) to give 2-(3-(3-(benzyloxy)phenyl)propyl)isoindoline-1,3-dione as a white solid. Yield (0.708 g, 55%): 1H NMR (400 MHz, DMSO-d6) δ 7.81-7.84 (m, 2H), 7.69-7.72 (m, 2H), 7.30-7.44 (m, 5H), 7.13-7.18 (m, 1H), 6.83-6.85 (m, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.74 (dd, J=7.8, 2.0, 1H), 5.03 (s, 2H), 3.74 (t, J=7.2 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 2.0-2.08 (m, 2H).

Aufarbeitung

  1. customInstead of a Mitsunobu reaction
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionextracted with DCM
  4. washwashed with water
  5. customdried over anhy
  6. filtrationFiltration and concentration under reduced pressure
  7. customgave the crude product, which
  8. customwas purified by flash chromatography (hexane-ethyl acetate (0-30%) gradients)

Quellen und Nachweise

ORD-Eintrag
ord-5b72be5d12984ac3b3ad52285c35b1d9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829244B2

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