Ethanol → Methyl 5-formylpyrazine-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH:11](Br)Br)=[CH:7][N:6]=1)=[O:4].C([OH:16])C>C1COCC1.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([CH:11]=[O:16])=[CH:7][N:6]=1)=[O:4]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
A solution of 5-dibromomethyl-pyrazine-2-carboxylic acid methyl ester (1.00 g, 3.23 mmol) in a mixture of ethanol (20 mL) and THF (10 mL) was heated to 80° C. A solution of silver nitrate (2.20 g, 12.9 mmol) in H2O (4 mL) was added. The reaction mixture was heated at 80° C. for 1.25 h and was filtered while hot. The filtrate was concentrated to yield the title compound (1.36 g). This material was carried to the next step without purification.
Workup
- temperatureThe reaction mixture was heated at 80° C. for 1.25 h
- filtrationwas filtered while hot
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-60f17a351a8d493e9d0d0c9fd77a0d26
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423147B2
Reaction notes
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