2-Iodophenol → 3-(2-(2-Iodophenoxy)ethyl)thiophene

HRID 84469

Reaktionsgleichung

Reaktionsgleichung von HRID 84469
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][S:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 107842-IodophenolHCID 83731Thiophene-3-ethanolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 640847853-(2-(2-Iodophenoxy)ethyl)thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

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. customReaction mixture
  2. customPurification on silica

Quellen und Nachweise

ORD-Eintrag
ord-558fc451011e4d648d8c02d6fa52669b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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