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

HRID 745981Notes

Reaction equation

HRID 745981 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 30215682-Naphthalenemethanol, 5,6-dihydro-7-(1H-imidazol-1-yl)-Yield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8a75f458bbff434ca54343361c987f47
Source dataset
uspto-grants-1986_07
Patent number
US04602022

Reaction notes

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