Imidazole → Trans-1-[6-(2,6-dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazole
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:10]=1[CH2:11][O:12][C@@H:13]1[O:18][C@@H:17]([CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:16][CH2:15][CH2:14]1.[I-].[Na+]>CN(C)C=O>[Cl:8][C:9]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:10]=1[CH2:11][O:12][C@@H:13]1[O:18][C@@H:17]([CH2:19][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)[CH2:16][CH2:15][CH2:14]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
196 mg of 55% sodium hydride were added to a solution of 306 mg of imidazole in 14 ml of dimethylformamide and the mixture was stirred at 80° C. for 30 minutes. The mixture was then cooled to room temperature, after which 1.335 g of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran and 450 mg of sodium iodide were added thereto; the mixture was then stirred at 80°-85° C. for 2 hours. At the end of this time, the mixture was treated and purified essentially as described in Example 1(b), to give 965 mg of the title compound in the form of a colourless oil.
Workup
- temperatureThe mixture was then cooled to room temperature
- stirringthe mixture was then stirred at 80°-85° C. for 2 hours
- additionAt the end of this time, the mixture was treated
- custompurified essentially
Sources & evidence
- ORD record
- ord-3e15df6b96a94f84889d4715648fdb85
- Source dataset
- uspto-grants-1983_12
- Patent number
- US04421758
Reaction notes
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