Sodium Hydroxide → 2-Methoxy-7-(4-methoxyphenyl)naphthalene

HRID 895162Notes

Reaction equation

HRID 895162 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[OH-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:18][O:17][C:11]1[CH:12]=[CH:13][C:14]2[C:9](=[CH:8][C:7]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 201262(4-Methoxyphenyl)boronic acidHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl ester

Product 1

HCID 117371492-Methoxy-7-(4-methoxyphenyl)naphthaleneYield 79.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-methoxy-2-naphthyl trifluoromethanesulfonate (3.15 g, 10.3 mmol), 4-methoxy-phenylboronic acid (2.2 g, 14 mmol) sodium carbonate (10 mL of 2N aqueous solution), tetrakis(triphenylphosphine)palladium (0.59 g, 0.05 mmol), and 100 mL ethylene glycol dimethyl ether were heated to reflux for 8 hr. The mixture was cooled to room temperature and poured into 100 mL of 1 N NaOH, The mixture was extracted with ethyl acetate (3×250 mL), washed with brine (2×100 mL), dried over magnesium sulfate, filtered, evaporation of the solvent and purification by silica chromatography (5%-10% ethyl acetate-hexanes) yielded 2.17 g (79%) of the title compound as a white solid: mp 154° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 3.94 (3H, s), 7.02 (2H, d, J=8.72 Hz), 7.13 (1H, dd, J=2.54 Hz, J=9.09 Hz), 7.18 (1H, d, J=2.55 Hz), 7.56 (1H, dd, J=1.82 Hz, J=8.36 Hz), 7.65 (2H, d, J=8.72 Hz), 7.74 (1H, d, J=9.09 Hz), 7.81 (1H, d, J=8.36 Hz), 7.89 (1H, d, J=1.09 Hz); MS (EI) m/z264 (M).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 8 hr
  3. extractionThe mixture was extracted with ethyl acetate (3×250 mL)
  4. washwashed with brine (2×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporation of the solvent and purification by silica chromatography (5%-10% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-c1c664949fab4e6198ecd67cd59c8773
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

Loading…