Cesium carbonate → 2-(2-(3-(1-Hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione

HRID 875568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875568
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[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]([CH:19]=[CH:20][CH:21]=2)[O:5][CH2:6][CH2:7][N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[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 580275342-[2-(3-Hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione

Produkt 1

HCID 673174532-(2-(3-(1-Hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The suspension of phenol 24 (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-(2-(3-(1-hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione as yellow oil. Yield (0.53 g, 35%): 1H NMR (400 MHz, CDCl3) δ 7.92-7.98 (m, 1H), 7.40-7.51 (m, 3H), 7.08-7.14 (m, 1H), 6.45-6.54 (m, 3H), 4.03 (s, 2H), 3.68-3.76 (m, 2H), 1.35-1.92 (m, 16H).

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-1cdb951cff32432586d8e48a1cc4d9d6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981153B2

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