Water → 3,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal
Reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[C:9](Br)=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1.C([Li])CCC.C([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=O.O.[O:31]1CCC[CH2:32]1>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[C:9]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[CH2:32][OH:31]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 6-bromo-3,4-dimethoxybenzaldehyde dimethyl acetal (20 ml) in tetrahydrofuran (100 ml) is cooled to -60° C., and thereto is added dropwise a 1.6 M solution of n-butyl lithium in hexane (45.1 ml) over a period of 20 minutes under nitrogen atmosphere. The mixture is reacted at the same temperature for 30 minutes, and thereto is added dropwise a solution of 4-formylpyridine (7.36 g) in tetrahydrofuran (50 ml) over a period of 20 minutes. The reaction mixture is reacted for one hour, and thereto are added water and ethyl acetate (200 ml). The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure to remove the ethyl acetate to give 3,4-dimethoxy-6-(4-pyridyl)hydroxymethylbenzaldehyde dimethyl acetal (15.4 g).
Workup
- customThe mixture is reacted at the same temperature for 30 minutes
- customThe reaction mixture is reacted for one hour
- customThe ethyl acetate layer is separated
- washwashed
- customdried
- concentrationconcentrated under reduced pressure
- customto remove the ethyl acetate
Sources & evidence
- ORD record
- ord-be86f9b8e25c439380ac94cc637eaf5e
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05969140
Reaction notes
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