Methyl iodide → (RS)-Naproxen methyl ester

HRID 1076878

Reaktionsgleichung

Reaktionsgleichung von HRID 1076878
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]2.[H-].[Na+].[CH3:20]OCCOC.CI>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:20])[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]2

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 90324Methyl 6-methoxynaphthalene-2-acetate

Produkt 1

HCID 529084(RS)-Naproxen methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 22 g. of methyl 2-(6-methoxy-2-naphthyl)acetate (prepared by treating 20.5 g. of 2-(6-methoxy-2-naphthyl)acetic acid with 4.5 g. of diazomethane in ether), and 2.5 g. of sodium hydride in 150 ml. of 1,2-dimethoxyethane; 25 g. of methyl iodide are added. The reaction mixture is allowed to stand for several hours; then it is diluted with ethanol followed by water and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered and evaporated to yield methyl 2-(6-methoxy-2-naphthyl)propionate.

Aufarbeitung

  1. additionTo a mixture of 22 g
  2. waitto stand for several hours
  3. extractionextracted with methylene chloride
  4. washwashed with water to neutrality
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-41e6bd6d13f041b9a28a38ed80560d29
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03958012

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