Imidazole → HCID 70388212, compound

HRID 868013Notes

Reaction equation

HRID 868013 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.C1(C)C=CC(S(O[CH2:18][CH:19]2[CH2:28][CH2:27][C:26]3[CH:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:22][C:21]=3[CH2:20]2)(=O)=O)=CC=1>CN(C)C=O>[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:18][CH:19]1[CH2:28][CH2:27][C:26]2[CH:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:22][C:21]=2[CH2:20]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 13882817HCID 13882817, compound

Product 1

HCID 70388212HCID 70388212, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.56 g of 50% sodium hydride was suspended in 60 ml of anhydrous dimethylformamide, and 0.79 g of imidazole was added thereto. The mixture was stirred at room temperature for 20 minutes and 4.5 g of ethyl 6-(p-toluenesulfonyloxymethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate was added portionwise thereto. The resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and the residue was extracted with chloroform. The extract was washed with water and dried over sodium sulfate and then concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of methanol and chloroform (2:98 by volume) for elution to give 2.31 g of ethyl 6-(1-imidazolylmethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate as a colorless oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 days
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe residue was extracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. additiona mixture of methanol and chloroform (2:98 by volume)
  9. washfor elution

Sources & evidence

ORD record
ord-46842c7ce0044ab5bfa7269774a6514e
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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