Tetrahydrofuran → 2-Methoxy-6-(4-methoxyphenyl)naphthalene

HRID 895169

Reaktionsgleichung

Reaktionsgleichung von HRID 895169
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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Mg]Br)=[CH:18][CH:17]=1.C1COCC1>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.Cl>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[CH:3]=2)[CH:8]=1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 787862-Bromo-6-methoxynaphthaleneHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthaleneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a mixture of 2-bromo-6-methoxynaphthalene (23.79 g, 100.3 mmol) and tetrakis(triphenylphosphine)palladium (5.8 g, 5 mmol) was added a solution of 4-methoxyphenylmagnesium bromide in THF (400 mL of 0.5 N solution, 200 mmol). The stirred solution was heated to reflux for 3 hr, cooled to RT, and stirred into 200 mL of 1 N HCl. The mixture was extracted with dichloromethane and filtered through a short silica plug with dichloromethane. The solvent was removed to yield a crude yellow solid which was further purified by silica chromatography (20-50% ethyl acetate-hexanes) to yield 25.68 g (97%) of the title compound as a white solid: mp 190° C.; 1H NMR (CDCl3): δ 3.86 (3H, s), 3.93 (3H, s), 7.01 (2H, d, J=8.57 Hz), 7.14-7.18 (2H, m), 7.63 (2H, d, J=8.50 Hz), 7.67 (1H, dd, J=1.68 Hz, J=8.73 Hz), 7.76-7.80 (2H, m), 7.91 (1H, d, J=0.94 Hz); MS (ESI) m/z265 (M+H)+.

Aufarbeitung

  1. temperatureThe stirred solution was heated
  2. temperatureto reflux for 3 hr
  3. extractionThe mixture was extracted with dichloromethane
  4. filtrationfiltered through a short silica plug with dichloromethane
  5. customThe solvent was removed
  6. customto yield a crude yellow solid which
  7. customwas further purified by silica chromatography (20-50% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0d5a6172b0e6496a80b27a6c8630eeb8
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914074B2

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