Sodium hydride → HCID 68294284, compound

HRID 1850077Notes

Reaction equation

HRID 1850077 reaction equation
[CH3:1][C:2]1[C:6](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:13])[NH:4][N:3]=1.[H-].[Na+].[CH2:16](Br)[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:16]([N:4]1[C:5]([CH3:13])=[C:6](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])[C:2]([CH3:1])=[N:3]1)[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 98116BromomethylstyreneHCID 68294109HCID 68294109, compound

Product 1

HCID 68294284HCID 68294284, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(E)-methyl 3-(3,5-dimethyl-1H-pyrazol-4-yl)acrylate (360 mg, 2 mmol) was dissolved in DMF (6 mL). Sodium hydride, (NaH 60% dispersion, 80 mg, 1 equiv) was added in small portions while maintaining the temperature at 0° C. The mixture was then stirred at room temperature for 1 h. The mixture was cooled to 0° C. and cinnamyl bromide (394 mg, 1 equiv) was added. The mixture was then stirred overnight at room temperature. It was quenched with 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 gradient of hexane/EtOAc (10:1 to 0:100 v/v). Fractions containing pure product were combined and the solvents were removed under reduced pressure to yield (E)-methyl 3-(1-cinnamyl-3,5-dimethyl-1H-pyrazol-4-yl)acrylate (401 mg, 68%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was then stirred overnight at room temperature
  3. customIt was quenched with 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. additionFractions containing pure product
  11. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-431fffc21881432b83a476979e39ca14
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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