Imidazole → 3-(2-Iodo-ethyl)-naphtho[1,2-b]furan

HRID 1768024Notes

Reaction equation

HRID 1768024 reaction equation
[O:1]1[CH:5]=[C:4]([CH2:6][CH2:7]O)[C:3]2[CH:9]=[CH:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[CH:13][CH:12]=3.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I.N1C=CN=C1>C1COCC1>[I:36][CH2:7][CH2:6][C:4]1[C:3]2[CH:9]=[CH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:2]=2[O:1][CH:5]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 236144482-(Naphtho[1,2-b]furan-3-yl)ethan-1-ol

Product 1

HCID 236144513-(2-Iodo-ethyl)-naphtho[1,2-b]furan

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-naphtho[1,2-b]furan-3-yl ethanol (1.06 g, 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. It 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 3-(2-iodo-ethyl)-naphtho[1,2-b]furan, was obtained as brown liquid. Yield: 1.4 g (87%); 322 (M+H).

Workup

  1. customquenched with water
  2. extractionIt 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-758964981b0442b7b2ed6a0c0c89f888
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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