Water → 2-Naphthalenemethanol, 5,6-dihydro-7-(1H-imidazol-1-yl)-

HRID 745981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745981
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([C:22](OCC)=[O:23])=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=[CH:8]1.O>C1COCC1>[N:7]1([C:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([CH2:22][OH:23])=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=[CH:8]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 30215662-Naphthalenecarboxylic acid, 5,6-dihydro-7-(1H-imidazol-1-yl)-, ethyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 30215682-Naphthalenemethanol, 5,6-dihydro-7-(1H-imidazol-1-yl)-Ausbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of LiAlH4 (202 mg) in dry THF (2.4 ml) a solution of 1,2-dihydro-3-(1-imidazolyl)-6-ethoxycarbonyl-naphthalene (2.8 g) in dry THF (22 ml) was added dropwise at 0° C. under nitrogen atmosphere. The reaction mixture was refluxed for 1 day and then stirred overnight at room temperature. H2O (40 ml) was added and the precipitate formed filtered off. The filtrate was concentrated, extracted with CHCl3, dried (Na2SO4) and evaporated under vacuum to give 1,2-dihydro-3-(1-imidazolyl)-6-hydroxymethyl-naphthalene (2 g), m.p. 88°-91° C.

Aufarbeitung

  1. additionwas added dropwise at 0° C. under nitrogen atmosphere
  2. temperatureThe reaction mixture was refluxed for 1 day
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. concentrationThe filtrate was concentrated
  6. extractionextracted with CHCl3
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8a75f458bbff434ca54343361c987f47
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04602022

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