Imidazole → 3-(2-Iodoethyl)-7-methoxy-1-benzofuran

HRID 1768006Notes

Reaction equation

HRID 1768006 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13]O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:34]I.N1C=CN=C1>C1COCC1>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][I:34])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 226629353-(2-Hydroxyethyl)-7-methoxybenzofuran

Product 1

HCID 236144473-(2-Iodoethyl)-7-methoxy-1-benzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(7-methoxy-1-benzofuran-3-yl)ethanol (960 mg, 5 mmol) in anhydrous THF (50 ml), triphenylphosphine (1.572 g, 6 mmol), iodine (1.518 g, 6 mmol) and imidazole (408 mg, 6 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 4 hrs and quenched with water. The reaction mixture was extracted with chloroform, washed well with 5% Na2S2O3 solution and the organic layer was dried over anhydrous MgSO4. It was filtered and concentrated. The residue was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexane. The product, namely 2-(7-methoxy-1-benzofuran-3-yl)ethyl iodide, was obtained as brown liquid. Yield: 1.3 g (86%); 302 (M+H).

Workup

  1. customquenched with water
  2. extractionThe reaction mixture was extracted with chloroform
  3. washwashed well with 5% Na2S2O3 solution
  4. dry with materialthe organic layer was dried over anhydrous MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated
  7. customThe residue was purified by silica-gel column chromatography
  8. washby eluting it with 30% ethyl acetate

Sources & evidence

ORD record
ord-551847be6c8a4b5c828b603fe1bbce0e
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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