Acetic Acid → 5-Tert-butyl-4,5-dihydro-3-(4,4-dimethyl-1,3-dioxopentyl)-4-oxo-imidazo[1,5-a]quinoxaline

HRID 1029401Notes

Reaction equation

HRID 1029401 reaction equation
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]2[CH:15]=[N:16][C:17]([C:18](OCC)=[O:19])=[C:7]2[C:6]1=[O:23])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].[H-].[Na+].C(O)(=O)C>O1CCCC1>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]2[CH:15]=[N:16][C:17]([C:18](=[O:19])[CH2:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[C:7]2[C:6]1=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6416PinacoloneHCID 24758Sodium hydrideHCID 19900389Ethyl 5-tert-butyl-4,5-dihydro-4-oxo-imidazo[1,5-a]quinoxaline-3-carboxylate

Product 1

HCID 199003905-Tert-butyl-4,5-dihydro-3-(4,4-dimethyl-1,3-dioxopentyl)-4-oxo-imidazo[1,5-a]quinoxaline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of ethyl 5-tert-butyl-4,5-dihydro-4-oxo-imidazo[1,5-a]quinoxaline-3-carboxylate (1.6 g, 5 mmol) and pinacolone (1.25 ml, 10 mmol) in dry tetrahydrofuran (THF) (30 ml) was added sodium hydride (200 mg, 80% in mineral oil, 6.9 mmol). The mixture was brought to reflux for 2 h, then cooled to room temperature and neutralized with acetic acid. After evaporation of the solvent the residue was partitioned between sat. aqueous NaHCO3 (10 ml) and methylene chloride (30 ml). The organic phase was dried over Na2SO4 and evaporated to give the title compound as yellow crystals. M.p. 190°-191 ° C. (Compound 1).

Workup

  1. temperatureto reflux for 2 h
  2. customAfter evaporation of the solvent the residue
  3. customwas partitioned between sat. aqueous NaHCO3 (10 ml) and methylene chloride (30 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-4c1d8d221f804d51885872518a851d69
Source dataset
uspto-grants-1992_04
Patent number
US05102885

Reaction notes

Loading…