Acetone → HCID 178440097, compound

HRID 265173Notes

Reaction equation

HRID 265173 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[N:7]=[C:8]([CH2:16][CH2:17][CH3:18])[NH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])[CH3:4].CC(C)=O>C(O)C>[OH:5][CH:3]([C:6]1[N:7]=[C:8]([CH2:16][CH2:17][CH3:18])[NH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 10513320HCID 10513320, compound

Product 1

HCID 178440097HCID 178440097, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

125 mg of sodium borohydride were added to a solution of 1.50 g of ethyl 4-acetyl-2-propylimidazole-5-carboxylate [prepared as described in step (ii) above] in 15 ml of ethanol, and the resulting mixture was stirred at room temperature for 30 minutes. 2 ml of acetone were added, and the mixture was stirred for a further 10 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, and the concentrate was dissolved in methanol. The solution was again concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using 1:20 and 1:10 by volume mixtures of methylene chloride and methanol as the eluent, to give 1.32 g of the title compound as crystals, melting at 151°-153° C.

Workup

  1. stirringthe mixture was stirred for a further 10 minutes
  2. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  3. dissolutionthe concentrate was dissolved in methanol
  4. concentrationThe solution was again concentrated by evaporation under reduced pressure
  5. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-7b73fef13c554fa29f29221080d356b4
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

Loading…