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

HRID 84470

반응식

HRID 84470 반응식
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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 5946Tetraethylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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. 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

출처 및 근거

ORD 기록
ord-7923b99daeb74876aea1a1cb1e406144
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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