Potassium Carbonate → 7-(2-Methoxy-ethoxy)-benzo[b]thiophene

HRID 1009011Notes

Reaction equation

HRID 1009011 reaction equation
[OH:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.I[CH2:12][CH2:13][O:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:15][O:14][CH2:13][CH2:12][O:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791361-Iodo-2-methoxyethaneHCID 110840501-Benzothiophen-7-ol

Product 1

HCID 673048817-(2-Methoxy-ethoxy)-benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7-hydroxy-benzo[b]thiophene (Boot, J. R.; Brace, G.; Delatour, C. L.; Dezutter, N.; Fairhurst, J.; Findlay, J.; Gallagher, P. T.; Hoes, I.; Mahadevan, S.; Mitchell, S. N.; Rathmell, R. E.; Richards, S. J.; Simmonds, R. G.; Wallace, L.; Whatton, M. A.; Bioorganic & Medicinal Chemistry Letters (2004), 14(21), 5395-5399; 1.0 g, 6.6 mmol) in acetone (15 mL) was added 2-iodoethyl methylether (Ubichem, CAS: 4296-15-5, 2.47 g, 13.2 mmol) and potassium carbonate (1.84 g, 13.2 g). The reaction mixture was stirred at reflux for 16 h, quenched with ice/water, and extracted with ethyl acetate. The organics were washed, dried and concentrated. The residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 7-(2-methoxy-ethoxy)-benzo[b]thiophene (1.29 g) as a colourless oil. MS (ISP): m/209.1 (M+H)+

Workup

  1. temperatureat reflux for 16 h
  2. customquenched with ice/water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c4c2136a9b824e6c9212a84629329dfe
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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