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

HRID 84469

반응식

HRID 84469 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customReaction mixture
  2. customPurification on silica

출처 및 근거

ORD 기록
ord-558fc451011e4d648d8c02d6fa52669b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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