Methyl iodide → 2-Methyl-2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

HRID 963720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963720
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[C:6]1=[O:17])=[O:4].[H-].[Na+].CI.[C:22](OCC)(=O)C>O1CCCC1.O>[CH3:22][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[C:6]1=[O:17]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 190824592-Methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 543642852-Methyl-2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene (3.9 g) in tetrahydrofuran (50 ml) were added NaH (0.73 g, 60% in oil) and then methyl iodide (3 ml) at 0° C. under N2. After being stirred for 1 hour at room temperature, the solution was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N--HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 2-methyl-2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene (4.0 g).

Aufarbeitung

  1. customat 0° C.
  2. washThe organic layer was washed with 1N
  3. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8619e4ad0e43426b9647ae11a1083bb6
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763489

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