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

HRID 905056Notes

Reaction equation

HRID 905056 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[CH2:4][O:5][C@@H:6]1[O:11][C@@H:10]([CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][CH2:8][CH2:7]1.[Na].[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CN(C)C=O>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[CH2:4][O:5][C@@H:6]1[O:11][C@@H:10]([CH2:12][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 5360545SodiumHCID 13073916trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

Product 1

HCID 13073918Trans-1-[6-(2,4-dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

As in Example 1(b), 5 ml of a dimethylformamide solution containing 1.70 g of trans-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran were added to 15 ml of a dimethylformamide solution containing 5.73 mmoles of the sodium salt of imidazole and the mixture was allowed to react for 2 hours at 85° C., after which it was treated and purified as in Example 1(b), to give 1.2 g of the title compound as a colourless oil.

Workup

  1. customto react for 2 hours at 85° C.
  2. additionafter which it was treated
  3. custompurified as in Example 1(b)

Sources & evidence

ORD record
ord-4520bceb7a934832a7057fe0012a15be
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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