Water → 1-[(E)-4-(2-naphthyl)-3-buten-1-yl]-1H-imidazole

HRID 2229253Notes

Reaction equation

HRID 2229253 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)O)[CH:5]=[CH:4][N:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(COC)OC>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1/[CH:9]=[CH:8]/[CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 18467047HCID 18467047, compound

Product 1

HCID 129730871-[(E)-4-(2-naphthyl)-3-buten-1-yl]-1H-imidazoleYield 26.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-(1H-imidazol-1-yl)-1-(2-naphthyl)-1-butanol (0.450 g) and p-toluenesulfonic acid hydrate (0.589 g) in dimethoxyethane (20 ml) was refluxed for 16 hours. To the mixture was added water, then the whole was concentrated and extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1) followed by crystallization from ethyl acetate-hexane to give the titled compound (0.112 g) as a colorless powder.

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationthe whole was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (ethyl acetate-MeOH=20:1)
  8. customfollowed by crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-355e4eb836264ec1ac4080633f01fce4
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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