Reaktion #171652

Reaktionsgleichung

3-[2-(2-iodo-phenoxy)-ethyl]-thiophene

potassium carbonate

→

4,5-dihydrobenzo[b]thieno[2,3-d]oxepine

Lösungsmittel

DMF

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas microwaved at 100° C. for 1 hour
2. 2
   Filtrationfiltered through celite
3. 3
   WaschenThe filtrate was washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated in-vacuo
6. 6
   SonstigePurification on silica

Vorschrift

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.

Quelle