Sodium Carbonate → HCID 20077584, compound

HRID 1655085Notes

Reaction equation

HRID 1655085 reaction equation
[CH2:1]([N:7]1[C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=[CH:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[CH2:1]([N:7]1[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[CH:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 20077582Methyl 1-hexyl-1H-imidazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20077584HCID 20077584, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the product of step (i) (420 mg, 2 mmol) in THF (15 ml) was added to a suspension of lithium aluminium hydride (380 mg, 10 mmol) in THF (15 ml) with stirring at 0° C. under argon. After 1 hour a saturated aqueous solution of sodium carbonate (1 ml) was added dropwise and the mixture was stirred for a further 15 minutes before being filtered through a pad of diatomaceous earth, washing well with ethyl acetate. The filtrate was evaporated to give 1-hexyl-5-hydroxymethylimidazole (349 mg, 96% yield) as a solid;

Workup

  1. stirringthe mixture was stirred for a further 15 minutes
  2. filtrationbefore being filtered through a pad of diatomaceous earth
  3. washwashing well with ethyl acetate
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-808cf8b25ce54d3eb553d8cc9beae5b0
Source dataset
uspto-grants-1995_04
Patent number
US05410064

Reaction notes

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