Pyridine → HCID 22481787, compound
Reaction equation
O/[N:2]=[CH:3]\[C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:3]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
E/Z-Methyl 2-[(hydroxyimino)methyl]-1-benzofuran-6-carboxylate (438 mg, 2.0 mmol) is suspended in CH2Cl2 (8 ml) in a dry flask under nitrogen. Pyridine (0.65 ml, 8.0 mmol) is added via syringe, and the mixture is cooled to 0° C. Trifluoroacetic anhydride (0.56 ml, 4.0 mmol) is added drop-wise, and the reaction is stirred overnight, allowing the ice bath to expire. The reaction is carefully quenched with saturated NaHCO3 (10 ml). The layers are separated and the organic layer is dried (K2CO3), filtered, and concentrated to a pink solid. The crude material is chromatographed over 25 g slurry-packed silica gel, eluting with 25% EtOAc/hexane. The appropriate fractions are collected and concentrated to afford 315 mg (78%) of methyl 2-cyano-1-benzofuran-6-carboxylate as a white solid.
Workup
- customThe reaction is carefully quenched with saturated NaHCO3 (10 ml)
- customThe layers are separated
- dry with materialthe organic layer is dried (K2CO3)
- filtrationfiltered
- concentrationconcentrated to a pink solid
- customThe crude material is chromatographed over 25 g slurry-packed silica gel
- washeluting with 25% EtOAc/hexane
- customThe appropriate fractions are collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8747185f749141dfae3fd56d0098df8f
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06894042B2
Reaction notes
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