Iodine → 6-Phenoxy-benzofuran-2-carboxylic acid ethyl ester

HRID 1171208Notes

Reaction equation

HRID 1171208 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].II.C[C:19]([CH3:22])([O-])[CH3:20].[K+].O.O1C[CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][C:20]3[CH:19]=[CH:22][CH:28]=[CH:27][CH:26]=3)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 807IodineHCID 962WaterHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 66786469Ethyl 6-hydroxybenzofuran-2-carboxylate

Product 1

HCID 576082856-Phenoxy-benzofuran-2-carboxylic acid ethyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of 6-hydroxy-benzofuran-2-carboxylic acid ethyl ester (200 mg, 967 μmol) in tetrahydrofuran (4 mL) and N,N-dimethylformamide (4 mL) were added diphenylindonium iodine (395 mg, 967 μmol) and potassium t-butoxide (109 mg, 967 μmol) at 0° C., which was stirred at room temperature for 40 minutes under nitrogen atmosphere. After further stirring for 3 hours at 60° C., water was added to the reaction solution at room temperature followed by extraction with ethyl acetate, washing the organic layer with sat. NaCl, drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the title compound (189 mg, 69%) as a colorless oil.

Workup

  1. stirringAfter further stirring for 3 hours at 60° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing the organic layer with sat. NaCl
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-e1afb6507601416fbe1eb0a6f16015eb
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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