Reaction equation
[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1.CC(=CC)C.O.Cl([O-])=[O:19].[Na+]>CC(O)(C)C>[I:1][C:2]1[C:7]([C:8]([OH:19])=[O:9])=[C:6]([O:10][CH3:11])[N:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-iodo-2-methoxynicotinaldehyde (1 g, 3.58 mmol) in t-BuOH (6 mL), cooled at 25° C., is added 2-methyl-2-butene (6 mL, 2 M solution), Na2HPO4 (1.2 g) and water (3 mL). The reaction mixture is stirred for 5 minutes and sodium chlorite (800 mg, 8.9 mmol) is added slowly. Stirring of the mixture is continued until the aldehyde is completely consumed (3 hours, monitored by LCMS). The reaction is quenched with aq. formic acid. The mixture is partitioned between ethyl acetate (100 mL) and the organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The white powder was used for the next reaction without any further purification. 1H NMR 400 MHz (DMSO-d6) δ 10.06 (s, 1H), 7.89 (d, 1H, J=5.6 Hz), 7.48 (d, 1H, J=5.6 Hz), 3.87 (s, 1H); MS m/z 294.1 (M+1). MS m/z 280.01 (M+1).
Workup
- stirringStirring of the mixture
- customis completely consumed (3 hours, monitored by LCMS)
- customThe reaction is quenched with aq. formic acid
- customThe mixture is partitioned between ethyl acetate (100 mL)
- washthe organic extracts are washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe white powder was used for the next reaction without any further purification
Sources & evidence
- ORD record
- ord-9a313dd65a38467894278503abdde5f1
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546370B2
Linked notes
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