Methanol → 1-(2-Chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

HRID 1740644

Reaktionsgleichung

Reaktionsgleichung von HRID 1740644
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([C:24](O)=[O:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([CH2:24][OH:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 220073981-(2-Chloro-4-pyridyl)-3-carboxy-6,7-diethoxynaphthalene

Produkt 1

HCID 220073461-(2-Chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 1-(2-chloro-4-pyridyl)-3-carboxy-6,7-diethoxynaphthalene in tetrahydrofuran (50 ml) is added dropwise a solution of 70% sodium aluminum bis(2-methoxyethoxy) hydride (70% toluene solution, 29.4 ml) in tetrahydrofuran (50 ml) at a temperature below 5° C. under nitrogen atmosphere, and the mixture is reacted at the same temperature for one hour. After the reaction is complete, to the mixture is added methanol (12 ml), and further thereto is added a 6.25 M aqueous sodium hydroxide solution (48 ml), and the mixture is stirred at 50° C. for one hour. The tetrahydrofuran layer is separated from the mixture, and the aqueous solution is extracted with methylene chloride, and the methylene chloride layer is separated, and combined with the tetrahydrofuran layer, then concentrated under reduced pressure. The resultant is extracted again with methylene chloride, washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1), and crystallized from ether to give 1-(2-chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene (3.94 g).

Aufarbeitung

  1. customthe mixture is reacted at the same temperature for one hour
  2. customThe tetrahydrofuran layer is separated from the mixture
  3. extractionthe aqueous solution is extracted with methylene chloride
  4. customthe methylene chloride layer is separated
  5. concentrationconcentrated under reduced pressure
  6. extractionThe resultant is extracted again with methylene chloride
  7. washwashed
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1)
  11. customcrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-7dc4719d2d8743f4b45b8d561d5bc40e
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05969140

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