Water → 1-{Trans-beta-[6-(2,4-dichlorobenzyloxy)tetrahydropyran-2-ylmethoxy]phenethyl}imidazole

HRID 905065Notes

Reaction equation

HRID 905065 reaction equation
[C:1]1([CH:7]([OH:14])[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:17][C:18]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:19]=1[CH2:20][O:21][C@@H:22]1[O:27][C@@H:26]([CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24][CH2:23]1.O>CN(C)C=O>[Cl:17][C:18]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:19]=1[CH2:20][O:21][C@@H:22]1[O:27][C@@H:26]([CH2:28][O:14][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 322392-(1H-imidazol-1-yl)-1-phenylethanolHCID 13073916trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

Product 1

HCID 542329281-{Trans-beta-[6-(2,4-dichlorobenzyloxy)tetrahydropyran-2-ylmethoxy]phenethyl}imidazoleYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 106 mg of 1-phenyl-2-(1-imidazolyl)ethanol in 1 ml of dimethylformamide was stirred with 5 mg of 55% sodium hydride at 50° C. for 30 minutes and the mixture was then left to cool at room temperature. To the resulting mixture were added 3 ml of a dimethylformamide solution containing 300 mg of trans-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, prepared as described in Example 2(a); the mixture was then stirred at 80° C. for 4 hours and then at 90° C. for 1 hour. At the end of this time, the reaction mixture was cooled, poured into water and extracted with diethyl ether. The ethereal extract was washed with water, dried over anhydrous sodium sulphate and then concentrated to evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 30:1 by volume mixture of ethyl acetate and triethylamine, to give 107 mg of the title compound as a liquid.

Workup

  1. waitthe mixture was then left
  2. customprepared
  3. waitat 90° C. for 1 hour
  4. temperatureAt the end of this time, the reaction mixture was cooled
  5. extractionextracted with diethyl ether
  6. extractionThe ethereal extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated to evaporation under reduced pressure
  10. customThe residue was purified by column chromatography through silica gel
  11. washeluted with a 30:1 by volume mixture of ethyl acetate and triethylamine

Sources & evidence

ORD record
ord-973a0cb948364a19884469d7b246b665
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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