Sodium hydride → HCID 57847059, compound

HRID 735726Notes

Reaction equation

HRID 735726 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1.[C:10]([O:16][CH2:17]Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]>O1CCCC1.CN(C=O)C>[C:10]([O:16][CH2:17][N:3]1[CH:7]=[C:6]([CH:8]=[O:9])[N:5]=[CH:4]1)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehydeHCID 87885Chloromethyl pivalate

Product 1

HCID 57847059HCID 57847059, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 1.0 g, 26 mmol) in tetrahydrofuran (10 ml) was added dropwise a solution of 1H-imidazole-4-carbaldehyde (1.92 g, 20 mmol) in DMF (5 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. Chloromethyl pivalate (3.92 g, 26 mmol) was further added dropwise at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (100 g), and eluted with hexane-ethyl acetate (4:1-1:2, v/v) to give the title compound (4.11 g, 98%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried (over anhydrous MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. washeluted with hexane-ethyl acetate (4:1-1:2

Sources & evidence

ORD record
ord-e9eb5ba35a8e48a5ba3fbaf16728e10e
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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