Cesium carbonate → HCID 22737360, Verbindung

HRID 51080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51080
[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.[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:21]=[CH:20][C:19]=1[O:30][CH2:31][CH2:32][CH2:33]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:27])([F:29])[F:28])[CH:21]=[CH:20][C:19]=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

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylateHCID 227373543-Bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether

Produkt 1

HCID 22737360HCID 22737360, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 40 ml DMF solution of ethyl 7-hydroxy-chromane-2-carboxylate (1.81 g, 8.15 mmol) and 3-bromopropyl 2-chloro-4-(2,2,2-trifluoroethoxy)phenyl ether (3.4 g, 9.8 mmol) was added cesium carbonate (3.2 g, 9.8 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on slica gel eluting with 20% AcOEt/hexanes to give the title compound 3.23 g (81%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and 2N hydrochloric acid
  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 slica gel
  9. washeluting with 20% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c41b1a77a6704e59a2c298e1a3132e1f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713508B2

Notizen zur Reaktion

Wird geladen…