Dimethylformamide → 6-Methoxy-2-naphthaldehyde
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.C([Li])CCC.CN(C)[CH:21]=[O:22]>C1COCC1>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:21]=[O:22])[CH:11]=[CH:10]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-bromo-6-methoxynaphthalene (0.5 g, 2.11 mmol) in THF (10 mL) at -78° C., was added n-butyllithium (1.69 mL of a 2.5 M in hexanes, 4.22 mmol) dropwise and the solution was stirred for 45 min at -78° C. N,N-dimethylformamide (0.31 g, 4.22 mmol) was then added and the reaction was allowed to stir for 15 min at -78° C. The reaction was quenched with saturated aqueous NH4Cl (10 mL). This solution was extracted with ethyl acetate (3×10 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 15:85) afforded 345 mg (88%) of 6-methoxy-2-napthaldehyde as an off-white solid.
Workup
- stirringto stir for 15 min at -78° C
- customThe reaction was quenched with saturated aqueous NH4Cl (10 mL)
- extractionThis solution was extracted with ethyl acetate (3×10 mL)
- dry with materialdried with MgSO4
- concentrationconcentrated
- customThe resulting residue was chromatographed (silica gel, ether:hexanes, 15:85)
Sources & evidence
- ORD record
- ord-3c442a353dc8467d9d59be3a9ddf22c6
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037853
Reaction notes
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