Water → 2-Naphthalenecarboxaldehyde, 8-ethyl-1-(methoxymethoxy)-
Reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([O:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8]2)[CH3:2].CN(C)[CH:19]=[O:20].O>CCOCC.CCCCCC.C([Li])CCC>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([O:13][CH2:14][O:15][CH3:16])=[C:10]([CH:19]=[O:20])[CH:9]=[CH:8]2)[CH3:2]Participants
Procedure
300 g of 8-ethyl-1-methoxymethoxynaphthalene was dissolved in 2.2 liters of absolute ether, in which 1.3 liters of a hexane solution of 1.6M n-butyl lithium was gently dropped at -20° C. in a stream of nitrogen. After the dropping, the solution was raised to room temperature and agitated for 2 hours. It was again cooled down to -40° C., to which 215 ml of N,N-dimethylformamide was added. After agitation for 30 minutes, 100 ml of water was added and the resultant organic phase was washed with a saturated saline solution. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 253 g of the captioned compound as colorless crystals.
Workup
- additionwas gently dropped at -20° C. in a stream of nitrogen
- additionwas added
- waitAfter agitation for 30 minutes
- washthe resultant organic phase was washed with a saturated saline solution
- dry with materialAfter drying with anhydrous magnesium sulfate
- distillationthe solvent was distilled off
- customthe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-178a02682e9c416993852c3f9da6b7d2
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134111
Reaction notes
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