Water → HCID 54300324, compound

HRID 1739397Notes

Reaction equation

HRID 1739397 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.[H-].[Na+].[N:18]1([C:23]2[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=2)[CH:22]=[CH:21][N:20]=[CH:19]1.O>C1COCC1>[N:18]1([C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[CH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 7365304-(1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 54300324HCID 54300324, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of diethylbenzylphosphonate were dissolved in 50 ml of dry THF under nitrogen gas flow. To this solution, were added 0.21 g of 60% NaH while cooling the solution with ice, and the resultant solution was then stirred for 2 hours at room temperature. After cooling the whole solution with ice, 0.75 g of 4-(imidazole-1-yl)benzaldehyde were added thereto and stirred for 48 hours at room temperature. The solution reacted was condensed under reduced pressure, added with water, and extracted with chloroform. The organic layer resulted was dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure. The residue obtained was purified by using silica gel column chromatography, for which chloroform is used for the developer, thereby affording 0.5 g of 4-(imidazole-1-yl)stilbene.

Workup

  1. temperaturewhile cooling the solution with ice
  2. additionwere added
  3. customThe solution reacted
  4. customcondensed under reduced pressure
  5. extractionextracted with chloroform
  6. customThe organic layer resulted
  7. dry with materialwas dried with anhydrous magnesium sulfate
  8. customthe solvent used was removed by distillation under reduced pressure
  9. customThe residue obtained
  10. customwas purified

Sources & evidence

ORD record
ord-f06e67d2950d484f99423178f02b1157
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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