2,4,6-Tris((dimethylamino)methyl)phenol → Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylate

HRID 479632

Reaktionsgleichung

Reaktionsgleichung von HRID 479632
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.[C:17]1([O:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33]Br)=[C:26]([CH2:35][CH2:36][CH3:37])[CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>>[CH2:35]([C:26]1[CH:25]=[C:24]([O:23][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:31][CH2:32][CH2:33][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1)[CH2:36][CH3:37]

Komponenten

5

Edukt 4

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 10796Cesium carbonateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylateHCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

Produkt 1

HCID 18772266Ethyl 7-(3-(2-propyl-4-phenoxyphenoxy)propoxy)-chromane-2-carboxylateAusbeute 76 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 50 ml round-bottom flask were added ethyl 7-hydroxychromane-2-carboxylate (100 mg, 0.45 mmol), 4-(3-bromopropoxy)-3-propylphenyl phenyl ether (U.S. Pat. No. 6,008,237) (188 mg, 0.54 mmol), cesium carbonate (176 mg, 0.54 mmol), and DMF 3 ml. The resulting suspension was stirred at 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Eluting with 10% AcOEt/hexanes gave the title compound as a pale yellow oil 167 mg (76%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and water
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washEluting with 10% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-de6e3a706af54bc49ab9fde730dd9b1b
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645997B2

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