Sodium hydride → Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

HRID 1072107

Reaktionsgleichung

Reaktionsgleichung von HRID 1072107
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C)C=O.O1CCCC1>[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 390995Methyl 6-hydroxy-2-naphthoate

Produkt 1

HCID 12085484Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

14 g (69 mmol) of methyl 6-hydroxynaph-thalene-2-carboxylate in 90 ml of dimethylformamide and 90 ml of tetrahydrofuran are introduced into a round-bottomed flask and under a nitrogen stream. 3.3 g (82 mmol) of sodium hydride at 60% are added in small portions. When the gas emission has ceased, 8.7 ml (76 mmol) of 2-methoxyethoxymethyl chloride are added and the reaction medium is stirred for 3 hours at room temperature. It is then poured into ice-cold water and extracted with ether. The organic phase is dried over magnesium sulphate, filtered and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a heptane and ethyl acetate (80/20) mixture and 17 g (85%) of the expected product are obtained in the form of a colorless oil.

Aufarbeitung

  1. additionIt is then poured into ice-cold water
  2. extractionextracted with ether
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated off
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a heptane and ethyl acetate (80/20) mixture and 17 g (85%) of the expected product
  9. customare obtained in the form of a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-eb23a3d8fea94d1780e4a9ebee2e96e5
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908939B2

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