Ethyl Acetate → 2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]acetic acid

HRID 1081310Notes

Reaction equation

HRID 1081310 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[C:9]=1[C:10](=[O:20])[C:11]1[CH:16]=[C:15]([I:17])[C:14]([OH:18])=[C:13]([I:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].C([O:33][C:34](=[O:36])[CH3:35])C>CC(C)=O>[CH2:1]([C:5]1[O:6][C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[C:9]=1[C:10](=[O:20])[C:11]1[CH:12]=[C:13]([I:19])[C:14]([O:18][CH2:35][C:34]([OH:36])=[O:33])=[C:15]([I:17])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 74769L-3373

Product 1

HCID 108973252-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]acetic acidYield 49.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-n-butyl-3-(3,5-diiodo-4-hydroxybenzoyl)benzofuran 1.0 g (1.83 mmol) and potassiumcarbonate 0.56 g (4 mmol) in aceton (dry) 100 ml, α-brom ethylacetate 1.0 g (12 mmol was added, and the solution was extracted with 100 ml water. The organic layer was evaporated to dryness and the yellow rest was dissolved in methanol 50 ml+1M NaOH 50 ml. The solution was heated to 50° C. for 15 h, extracted with 3×75 ml dichloromethane, and dried (MgSO4). Evaporating the solution and purification on silica gave 0.55 g (005).

Workup

  1. additionwas added
  2. extractionthe solution was extracted with 100 ml water
  3. customThe organic layer was evaporated to dryness
  4. dissolutionthe yellow rest was dissolved in methanol 50 ml+1M NaOH 50 ml
  5. extractionextracted with 3×75 ml dichloromethane
  6. dry with materialdried (MgSO4)
  7. customEvaporating
  8. customthe solution and purification on silica

Sources & evidence

ORD record
ord-36b37858151a42fd8facdaf2a2abe40d
Source dataset
uspto-grants-1996_12
Patent number
US05585404

Reaction notes

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