Cesium carbonate → 2-(3-(3-((1-Hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione

HRID 875567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875567
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[O:22]1[C:24]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[OH:22][C:24]1([CH2:23][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[CH:5]=[CH:6][CH:7]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 132407571-Oxaspiro[2.7]decaneHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Produkt 1

HCID 673176112-(3-(3-((1-Hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of the phenol 58 (1.0 g, 3.5 mmol), 1-oxa-spiro[2.7]decane (0.5 g, 3.2 mmol) and Cs2CO3 (1.14 g, 3.5 mmol) in DMSO (4 mL) was heated at 120° C. for 16 h. After completion of reaction, the mixture was quenched by the addition of 1N HCl and extracted with DCM. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (0 to 10% 7N NH3/methanol-CH2Cl2) afforded 2-(3-(3-((1-hydroxycyclooctyl)methoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (1.057 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.10-7.36 (m, 2H), 6.40-6.80 (m, 6H), 3.69 (s, 2H), 2.10-2.45 (m, 2H), 1.30-2.0 (m, 18H).

Aufarbeitung

  1. customAfter completion of reaction
  2. customthe mixture was quenched by the addition of 1N HCl
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0 to 10% 7N NH3/methanol-CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-05f7707efe134e9c982d374d13b0e435
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981153B2

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