Water → HCID 67119243, compound

HRID 2076698Notes

Reaction equation

HRID 2076698 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C(=O)([O-])[O-].[Cs+].[Cs+].O.C([N:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[N:18][N:17]=[N:16]1)C=C>CN(C)C=O>[CH2:1]([N:16]1[N:17]=[N:18][C:19]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[N:15]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 67119354HCID 67119354, compound

Product 1

HCID 67119243HCID 67119243, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl bromide (0.27 ml, 3.13 mmol) and cesium carbonate (1.02 g, 3.13 mmol) were added to a solution of the obtained compound in N,N-dimethylformamide (5 ml), and the mixture was stirred at room temperature for 1 hour. After water was added to the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1) to give a mixture of 1-allyl-5-(4′-methoxymethoxy-1,1′-biphenyl-4-yl)-1H-tetrazole and 2-allyl-5-(4′-methoxymethoxy-1,1′-biphenyl-4-yl)-2H-tetrazole (504 mg, two-step total yield: 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous NaCl solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1)
  7. customto give

Sources & evidence

ORD record
ord-4a267acc3a054a589f62dd5da9ee4939
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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