1-Bromo-3-methylbutane → HCID 22319424, compound

HRID 497572Notes

Reaction equation

HRID 497572 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1C=O.Br[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14].C1OCCOCCOCCOCCOCC[O:18][CH2:17]1>O1CCCC1>[CH2:11]([N:5]1[CH:6]=[C:7]([CH:17]=[O:18])[N:3]=[CH:4]1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 249551H-imidazole-2-carbaldehydeHCID 2855718-Crown-6

Product 1

HCID 22319424HCID 22319424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (20 g, 60% dispersion in mineral oil, 0.5 mol) in tetrahydrofuran (300 ml) was cooled to 0° C., and 2-imidazolecarboxaldehyde (45 g, 0.47 mol) was added portionwise over 30 minutes. Once addition was complete, the reaction was stirred at 0° C. for 30 minutes, then allowed to warm to room temperature. 1-Bromo-3-methylbutane (60.8 ml, 0.5 mol) and 18-crown-6 (140 mg) were added, and the reaction was heated at reflux for 18 hours. The cooled reaction was quenched by the addition of water (400 ml), and the resulting mixture extracted with dichloromethane (800 ml in total). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure. The residual orange oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane:methanol (40:60:0 to 100:0:0 to 98:0:2) to afford the title compound, 19.6 g.

Workup

  1. additionOnce addition
  2. temperatureto warm to room temperature
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 18 hours
  5. customThe cooled reaction
  6. customwas quenched by the addition of water (400 ml)
  7. extractionthe resulting mixture extracted with dichloromethane (800 ml in total)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. customevaporated under reduced pressure
  10. customThe residual orange oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane:methanol (40:60:0 to 100:0:0 to 98:0:2)

Sources & evidence

ORD record
ord-d051705ac0604e0aa9605048f311ae22
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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