Cesium carbonate → Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate

HRID 51075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51075
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]2)=[CH:8][CH:7]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[C:29]2[CH:30]=[CH:31][C:32]([OH:37])=[C:33]([CH2:34][CH2:35][CH3:36])[C:28]=2[O:27][N:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:39][C:24]([F:23])([F:38])[C:25]1[C:29]2[CH:30]=[CH:31][C:32]([O:37][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:15]=[C:14]4[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]4)=[CH:8][CH:7]=3)=[C:33]([CH2:34][CH2:35][CH3:36])[C:28]=2[O:27][N:26]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 22737362Ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylateHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Produkt 1

HCID 69898123Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 2 ml DMF solution of ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylate (40 mg, 0.108 mmol) and 3-trifluoromethyl-7-propyl-6-hydroxybenzisoxazole (U.S. Pat. No. 6,090,836) (29 mg, 0.118 mmol) was added cesium carbonate (39 mg, 0.12 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 water. 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 silica gel. Elution with 20% AcOEt/hexanes gave the title compound as a pale yellow oil 49 mg (85%).

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. washElution with 20% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0f682bf914234a3cb79023e25a704622
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713508B2

Notizen zur Reaktion

Wird geladen…