Methyl iodide → 2-Methoxy-6-(4-methoxyphenyl)-1-methylnaphthalene

HRID 895185Notes

Reaction equation

HRID 895185 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1Br.[CH2:22]([Li])CCC.CN(CCN(C)C)C.IC>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[CH3:22]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 111636961-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 114031912-Methoxy-6-(4-methoxyphenyl)-1-methylnaphthaleneYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-6-(4-methoxyphenyl)-1-bromonaphthalene in THF (25 mL) at 0° C. was slowly added n-butyl lithium (2 mL of 2.5N) and TMEDA (0.60 g, 5.13 mmol, freshly distilled from KOH). After thirty minutes at 0° C. iodomethane (7.3 g, 51.3 mmol, passed through basic alumina) was added and the stirring solution was allowed to warm to room temperature overnight. The reaction was poured into water (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water, dried over magnesium sulfate, filtered, evaporation of the solvent, and purification by silica column chromatography (5% THF-hexanes) yielded 0.63 g (88%) of a white solid: mp 136-138° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 3.96 (3H, s), 7.02 (2H, d, J=8.74 Hz), 7.29 (1H, d, J=9.01 Hz), 7.60-7.80 (4H, m), 7.95 (1H, d, J=1.76 Hz), 8.00 (1H, d, J=8.86 Hz); MS (ESI) m/z279 (M+H)+.

Workup

  1. customat 0° C.
  2. distillationfreshly distilled from KOH)
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporation of the solvent, and purification by silica column chromatography (5% THF-hexanes)

Sources & evidence

ORD record
ord-905d31e87e4142679214364a8ebe6726
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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