Sodium Carbonate → 5-Benzofurancarboxylic acid, 3-methyl-, methyl ester
Reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1I)[CH:2]=[CH2:3].C([O-])([O-])=O.[Na+].[Na+].C([O-])=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].O.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:3][C:2]1[C:6]2[CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:13]=[CH:14][C:5]=2[O:4][CH:1]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Methyl 4-(allyloxy)-3-iodobenzoate (587 mg, 1.84 mmol) is combined with Pd(OAc)2 (5%, 20 mg, 0.1 mmol), Na2CO3 (487 mg, 4.6 mmol), sodium formate (125 mg, 1.8 mmol) and n-Bu4NCl.H2O (561 mg, 2.0 mmol) in DMF (5 mL) and heated to 80° C. for 2 days. The mixture is concentrated under high vacuum and partitioned between 50% saturated NaCl (10 mL) and CH2Cl2 (4×10 mL). The combined organics are washed with 5% HCl (10 mL), dried (Na2SO4) and concentrated to a brown oil. The crude material is chromatographed over 15 g slurry-packed silica gel, eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 153 mg (44%) of methyl 3-methyl-1-benzofuran-5-carboxylate as a white solid. HRMS (FAB) calcd for C11H10O3+H: 191.0708, found: 191.0705 (M+H)+.
Workup
- concentrationThe mixture is concentrated under high vacuum
- custompartitioned between 50% saturated NaCl (10 mL) and CH2Cl2 (4×10 mL)
- washThe combined organics are washed with 5% HCl (10 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated to a brown oil
- customThe crude material is chromatographed over 15 g slurry-packed silica gel
- washeluting with 15% EtOAc/hexane
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0820c17c70d247a2b6cf891106a258d1
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06894042B2
Reaction notes
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