Potassium Carbonate → 4,5-Dihydrobenzo[b]thieno[2,3-d]oxepine

HRID 84470

Reaktionsgleichung

Reaktionsgleichung von HRID 84470
I[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][C:7]1[CH:11]=[CH:10][S:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:9]1[C:8]2[C:2]3[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=3[O:4][CH2:5][CH2:6][C:7]=2[CH:11]=[CH:10]1

Komponenten

7

Edukt 2

HCID 11430Potassium CarbonateHCID 640847853-(2-(2-Iodophenoxy)ethyl)thiophene

Produkt 1

HCID 579001554,5-Dihydrobenzo[b]thieno[2,3-d]oxepine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 5946Tetraethylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-iodophenol (6.7 g, 30.6 mmol), 2-(3-thienyl)ethanol (3.57 g, 27.8 mol) and triphenylphosphene (8.00 g, 30.6 mmol) in THF, was slowly added a solution of DEAD (4.8 ml, 30.6 mmol). Reaction mixture was stirred at room temperature for 3 hours. Purification on silica gave 3-[2-(2-iodo-phenoxy)-ethyl]-thiophene. A mixture of 3-[2-(2-iodo-phenoxy)-ethyl]-thiophene (1.55 g, 4.69 mmol), palladium(II) acetate (105 mg, 0.47 mmol), potassium carbonate (3.2 g, 23.45 mmol), triphenylphosphene (246 mg, 0.94 mmol) and tetraethylammonium chloride (1.3 g, 4.69 mmol) in DMF was microwaved at 100° C. for 1 hour. The reaction was diluted with dichloromethane and filtered through celite. The filtrate was washed with water, dried (MgSO4), and concentrated in-vacuo. Purification on silica gave 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine.

Aufarbeitung

  1. customwas microwaved at 100° C. for 1 hour
  2. filtrationfiltered through celite
  3. washThe filtrate was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in-vacuo
  6. customPurification on silica

Quellen und Nachweise

ORD-Eintrag
ord-7923b99daeb74876aea1a1cb1e406144
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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