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

HRID 627897Notes

Reaction equation

HRID 627897 reaction equation
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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-04b4478d76a64b0690c3ee7cb82a0d0c
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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