Methanol → {3-[2-(2,4-Dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-phenyl}-acetic acid

HRID 29256Notes

Reaction equation

HRID 29256 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:30]=[CH:29][C:14]3[C:15]([CH3:28])=[C:16]([C:18](=[O:27])[C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[O:17][C:13]=3[CH:12]=2)[CH:6]=1.CO.O.[OH-].[Li+]>O1CCCC1>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:18]([C:16]1[O:17][C:13]2[CH:12]=[C:11]([C:7]3[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[CH:10]=[CH:9][CH:8]=3)[CH:30]=[CH:29][C:14]=2[C:15]=1[CH3:28])=[O:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59788899{3-[2-(2,4-Dichloro-benzoyl)3-methyl-benzofuran-6-yl]-phenyl}-acetic acid methyl ester

Product 1

HCID 59788959{3-[2-(2,4-Dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-phenyl}-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

{3-[2-(2,4-Dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-phenyl}-acetic acid methyl ester (3160 mg, 6.97 mmol) was dissolved in tetrahydrofuran (50 mL), methanol (20 mL), water (10 mL), and lithium hydroxide (2650 mg, 110.65 mmol) was added to the solution. The mixture was heated at 50° C. for 3 h then cooled to room temperature. The volatile components were removed under vacuum and the pH of the resulting aqueous component was adjusted to 1 with HCl (1N). The aqueous layer was extracted several times with ethyl acetate and the combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure. The crude residue was purified by MPLC with a gradient of 0 to 30% methanol/dichloromethane to give {3-[2-(2,4-dichloro-benzoyl)-3-methyl-benzofuran-6-yl]-phenyl}-acetic acid as a brown solid (2540 mg, 52% two steps). MS LC-MS (MH+439.1/441.1).

Workup

  1. temperaturethen cooled to room temperature
  2. customThe volatile components were removed under vacuum
  3. extractionThe aqueous layer was extracted several times with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure
  5. customThe crude residue was purified by MPLC with a gradient of 0 to 30% methanol/dichloromethane

Sources & evidence

ORD record
ord-27b2470b7bf24dadae8e60f0bc13d3b1
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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