Methyl iodide → 5-Methoxy-2-(4-methoxy-phenyl)-4-methyl-benzofuran

HRID 1794549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794549
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].[CH2:21]([Li])CCC.CN(CCN(C)C)C.IC>C1COCC1.O>[CH3:20][O:19][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[C:2]=1[CH3:21]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 102152694-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuranHCID 178418339Butyllithium

Produkt 1

HCID 101715395-Methoxy-2-(4-methoxy-phenyl)-4-methyl-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran 133 (0.282 g, 0.85 mmol) was taken into 20 mL of THF and cooled to 0° C. Then butyllithium (0.68 mL of a 2.5M solution in THF, 1.7 mmol) was added dropwise and allowed to stir for 20 minutes. Then TMEDA (0.256 mL, 1.7 mmol) was added followed by iodomethane (1.06 mL, 17 mmol). The reaction was allowed to stir overnight at room temperature. The reaction was poured into water and extracted with ethyl acetate. The combined organics was washed with water (2×), brine (1×), dried over magnesium sulfate filtered and concentrated. The resulting material was purified by column chromatography on silica gel, using a gradient of 1% to 3% ethyl acetate in hexane. The first fractions contained the product and another side product. This fraction was added to another synthesis of this compound (starting with 0.250 g 4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran) for the final cleavage reaction.

Aufarbeitung

  1. stirringto stir overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organics was washed with water (2×), brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was purified by column chromatography on silica gel
  8. additionThis fraction was added to another synthesis of this compound (starting with 0.250 g 4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran) for the final
  9. customcleavage reaction

Quellen und Nachweise

ORD-Eintrag
ord-1f0ea4d5433d4c08bd5bb38601196b67
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022733B2

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