Sodium hydride → HCID 86702819, compound

HRID 1850058Notes

Reaction equation

HRID 1850058 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1.Br[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[O:13]([CH2:12][CH2:11][N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68526Benzene, (2-bromoethoxy)-HCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 86702819HCID 86702819, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 6.3 g, 1.0 eq) was added to a solution of 1H-pyrazole-4-carbaldehyde (15 g, 156 mmol) in DMF (150 ml) at 0° C. The mixture was allowed to warm and was stirred at room temperature. (2-Bromoethoxy)benzene (30.2 g, 1 eq) was then added and the resulting mixture was stirred overnight at room temperature. It was quenched by addition of aqueous ammonium chloride, diluted with water and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography using a hexane/EtOAc gradient (10:1 to 0:100). Pure fractions were combined and evaporated under reduced pressure to yield 1-(2-phenoxyethyl)-1H-pyrazole-4-carbaldehyde (24 g, 71%).

Workup

  1. temperatureto warm
  2. stirringthe resulting mixture was stirred overnight at room temperature
  3. customIt was quenched by addition of aqueous ammonium chloride
  4. additiondiluted with water
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-74a6fc61721f40fda6d1f70fbf4b40a1
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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