Sodium hydride → 1-(Cyclopropylmethyl)-1H-pyrazole-4-carboxaldehyde

HRID 220483Notes

Reaction equation

HRID 220483 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.[H-].[Na+].Br[CH2:11][CH:12]1[CH2:14][CH2:13]1>CN(C=O)C>[CH:12]1([CH2:11][N:1]2[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 627265101-(Cyclopropylmethyl)-1H-pyrazole-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Add 1H-pyrazole-4-carbaldehyde (0.200 g, 2.08 mmol) to a suspension of sodium hydride (0.092 g, 2.29 mmol) in DMF (3 mL) at 0° C. Stir for 20 min. at 0° C. Add a solution of 1-(bromomethyl)cyclopropane (0.295 g, 2.18 mmol) in DMF (4 mL) dropwise to the reaction mixture. Stir reaction to ambient temperature for 18 hr. Quench with aqueous saturated sodium bicarbonate solution and add ethyl acetate. Separate organic layer. Extract aqueous layer twice with ethyl acetate, dry combined organics (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 60:40 ethyl acetate:hexanes) to give the title preparation (175 mg, 56%). GC-MS: m/z=150 [M+].

Workup

  1. stirringStir
  2. customreaction to ambient temperature for 18 hr
  3. customQuench with aqueous saturated sodium bicarbonate solution
  4. additionadd ethyl acetate
  5. dry with materialExtract aqueous layer twice with ethyl acetate, dry combined organics (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 60:40 ethyl acetate:hexanes)
  10. customto give the title
  11. custompreparation (175 mg, 56%)

Sources & evidence

ORD record
ord-5c741acd0a6c40dc8322e9cafc3c3750
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

Loading…