Dimethylformamide → 6-Methoxy-2-naphthaldehyde

HRID 2082094Notes

Reaction equation

HRID 2082094 reaction equation
C([Li])CCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.CN(C)[CH:21]=[O:22]>C1COCC1>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:21]=[O:22])[CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418339Butyllithium

Product 1

HCID 769916-Methoxy-2-naphthaldehydeYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of butyllithium (50.6 ml of a 2.5M solution in hexanes, 126.5 mmol) in THF (200 mL) at -78° C., was added 2-bromo-6-methoxynaphthalene (15.00 g, 63.3 mmol) portionwise. Upon completion of addition, the mixture was stirred for 30 min at -78° C. N,N-Dimethylformamide (6.94 g, 94.95 mmol) was added dropwise. The cooling bath was withdrawn and the reaction allowed to warm to ambient temperature. It was then quenched with saturated aqueous NH4Cl (200 mL) and the THF was stripped off in vacuo. The aqueous residue was extracted with ethyl acetate (3×200 mL). The organics were combined, dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; 1:4 ether, hexanes) to afford 8.86 g (75%) of 6-methoxy-2-naphthalenecarboxaldehyde as a pale yellow solid.

Workup

  1. additionUpon completion of addition
  2. customThe cooling bath was withdrawn
  3. temperatureto warm to ambient temperature
  4. customIt was then quenched with saturated aqueous NH4Cl (200 mL)
  5. extractionThe aqueous residue was extracted with ethyl acetate (3×200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was chromatographed (silica gel; 1:4 ether, hexanes)

Sources & evidence

ORD record
ord-f99df4ed5afe4910a167085f1b81747a
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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