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

HRID 84470

反応式

HRID 84470 の反応式
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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 5946Tetraethylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7923b99daeb74876aea1a1cb1e406144
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

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