Sodium Hydroxide → 5-[[4-(4-methylphenyl)phenoxy]methyl]furan-2-carboxylic Acid
Reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)=[O:4].[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[OH-].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:7]3[O:6][C:5]([C:3]([OH:2])=[O:4])=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)=[CH:22][CH:21]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester (Intermediate 6; 100 mg, 0.28 mmol), 4-methyl-phenyl-boronic acid (42 mg, 0.31 mmol), sodium hydroxide (45 mg, 1.13 mmol), palladium(II) acetate (2 mg, 0.01 mmol) and water (10 mL) was heated at ˜50° C. overnight. The mixture was filtered and the residue was washed with water, ethyl acetate, methylene chloride, and methanol. The aqueous layer was acidified and extracted three times with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried (magnesium sulfate), filtered, and evaporated to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (80 mg, 84%) as a white solid.
Workup
- filtrationThe mixture was filtered
- washthe residue was washed with water, ethyl acetate, methylene chloride, and methanol
- extractionextracted three times with ethyl acetate
- washThe combined organic layers were washed with water and saturated brine
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c33871ce1c4e4eb08a95031ea1388cb6
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07355049B2
Reaction notes
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