Imidazole → Trans-1-{6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]tetrahydropyran-2-ylmethyl}imidazole

HRID 905063

Reaction equation

HRID 905063 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:24][C@@H:25]2[O:30][C@@H:29]([CH2:31]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:28][CH2:27][CH2:26]2)[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:11][CH:10]=1.[I-].[Na+]>CN(C)C=O.O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([O:24][C@@H:25]2[O:30][C@@H:29]([CH2:31][N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[CH2:28][CH2:27][CH2:26]2)[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 53867744Trans-6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran

Product 1

HCID 13073922Trans-1-{6-[alpha-(4-chlorophenyl)-2,4-dichlorobenzyloxy]tetrahydropyran-2-ylmethyl}imidazoleYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

114 mg of 55% sodium hydride were added to a solution of 323 mg of imidazole in 10 ml of dimethylformamide, and, after the mixture had been stirred at 80° C. for 30 minutes, it was cooled to room temperature. There were then added 2.20 g of trans-6-[α-(4-chlorophenyl)-2,4-dichlorobenzyloxy]-2-tosyloxymethyltetrahydropyran, dissolved in 15 ml of dimethylformamide, and then 594 mg of sodium iodide were added to the mixture. The resulting mixture stirred under a stream of nitrogen at 90°-95° C. for 4 hours, after which it was cooled, diluted with water and extracted with diethyl ether. The ethereal extract was washed with water and dried over sodium sulphate, after which it was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography through silica gel eluted with a 8:1:0.1 by volume mixture of ethyl acetate, benzene and triethylamine, to give 1.346 g of the title compound as a colourless oil.

Workup

  1. temperatureit was cooled to room temperature
  2. stirringThe resulting mixture stirred under a stream of nitrogen at 90°-95° C. for 4 hours
  3. temperatureafter which it was cooled
  4. extractionextracted with diethyl ether
  5. extractionThe ethereal extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationafter which it was concentrated by evaporation under reduced pressure
  9. customthe residue was purified by column chromatography through silica gel
  10. washeluted with a 8:1:0.1 by volume mixture of ethyl acetate, benzene and triethylamine

Sources & evidence

ORD record
ord-480fb030c2094e639f142434abd29276
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Linked notes

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