Tributylstannane → Ethyl 2,3-dihydrobenzo[1,2-b]furan-3-acetate

HRID 963212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963212
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[O:8]1[CH2:9][CH:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 2

HCID 5948TributylstannaneHCID 54124865Ethyl 4-(2-bromophenyloxy)but-2-enoate

Produkt 1

HCID 12171952Ethyl 2,3-dihydrobenzo[1,2-b]furan-3-acetateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To ethyl 4-(2-bromophenyloxy)but-2-enoate (6.10 g, 21.0 mmol) in benzene (200 mL) at reflux was added AIBN (0.07 g, 0.4 mmol) followed by dropwise addition of a benzene (~65 mL) solution containing tri-n-butyltin hydride (6.72 g, 23.1 mmol). After complete addition (one h) the reaction was refluxed an additional 2 h. The reaction was concentrated in vacuo and the residue treated with Et2O (~50 mL) and a 60% KF solution (~40 mL). The solution was stirred 14 h. The precipitate was removed by filtration and the Et2O phase decanted off. The remaining aqueous phase was extracted with Et2O (3×). The combined Et2O solutions were washed with saturated aqueous NaCl solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (95:5 Hexane:EtOAc) afforded the title compound (4.12 g, 88%).

Aufarbeitung

  1. additionAfter complete addition (one h) the reaction
  2. temperaturewas refluxed an additional 2 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe residue treated with Et2O (~50 mL)
  5. customThe precipitate was removed by filtration
  6. customthe Et2O phase decanted off
  7. extractionThe remaining aqueous phase was extracted with Et2O (3×)
  8. washThe combined Et2O solutions were washed with saturated aqueous NaCl solution
  9. dry with materialdried with anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8b33b4c97a944f37ae7b194705104f1e
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763444

Notizen zur Reaktion

Wird geladen…