Reaction equation
Br[C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16].CCCCCC.C([Li])CCC.CN(C)[CH:30]=[O:31].O>O1CCCC1>[CH:30]([C:2]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:15][CH3:16])=[O:31]Participants
Procedure
A solution of 5.0 g (17.8 mmol) of 2-bromo-1,4-dimethoxy-3-methylnaphthalene in 30 ml of tetrahydrofuran was cooled to -78° C., to which 11.2 ml (17.9 mmol) of 1.6M n-butyllithium hexane solution was added dropwise, and stirred at the same temperature for 10 minutes after completion of the addition. Then 1.3 g (17.8 mmol) of dimethylformamide was added dropwise to the reaction mixture, and stirred at room temperature for 1 hour after completion of the addition. Water was added to the reaction mixture, from which the product was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2), and crystallized from hexane-isopropyl ether, to give 2.0 g (48.9%) of 2-formyl-1,4-dimethoxy-3-methylnaphthalene. m.p. 95°-96° C.
Workup
- additionwas added dropwise
- additionafter completion of the addition
- stirringstirred at room temperature for 1 hour
- additionafter completion of the addition
- extractionwas extracted with ethyl acetate
- washThe extract was washed with water
- customdried
- concentrationconcentrated
- customThe residue was purified with silica gel column chromatography (hexane-isopropyl ether (8:2)
- customcrystallized from hexane-isopropyl ether
Sources & evidence
- ORD record
- ord-78bfad3750a0479ca2aeea767dc20a24
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05229385
Linked notes
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