Potassium Iodide → {4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-acetic acid methyl ester

HRID 599705Notes

Reaction equation

HRID 599705 reaction equation
[CH2:1]([C:3]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH3:24])[CH:18]=1)([C:6]1[S:10][C:9]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:30][O:29][C:27](=[O:28])[CH2:26][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:3]([CH2:4][CH3:5])([C:6]2[S:10][C:9]3[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=3[CH:7]=2)[CH2:1][CH3:2])=[CH:18][C:19]=1[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 672728104-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenol

Product 1

HCID 57835409{4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-acetic acid methyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-[1-ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenol (2.53 g, 7.43 mmol) and acetonitrile (25 mL) is added methyl bromoacetate (0.84 mL, 8.92 mmol), powdered potassium carbonate (4.10 g, 29.72 mmol), and potassium iodide (0.12 g, 0.74 mmol). The resulting slurry is stirred at reflux temperature for 2 h, filtered, and concentrated. The residue is dissolved in diethyl ether (100 mL), washed with water (75 ml), brine (75 mL), dried over MgSO4, filtered, and concentrated to give the title compound (1.5 g, 3.63 mmol, 49%). 1H NMR (CDCl3), δ 0.74 (t, J=7.2 Hz, 6H), 2.17 (q, J=14.7, 7.5 Hz, 4H), 2.25 (s, 3H), 2.30 (s, 2H), 3.80 (s, 3H), 3.86 (s, 3H), 3.60 (d, J=8.6 Hz, 1H), 6.89 (dd, J=8.6, 2.5 Hz, 1H), 7.04 (s, 1H), 7.07 (s, 1H), 7.16 (d, J=2.5 Hz, 1H), 7.55 (d, J=8.9 Hz, 1H).

Workup

  1. temperatureat reflux temperature for 2 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in diethyl ether (100 mL)
  5. washwashed with water (75 ml), brine (75 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d07967a8ab114aa1aec79c45ff987b08
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

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