Acetic Acid → Quinoxaline-2-carbaldehyde

HRID 2187383Notes

Reaction equation

HRID 2187383 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11](OCC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C>O1CCCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH:11]=[O:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5827017065-23-8HCID 21226445Aluminium lithium hydride

Product 1

HCID 594088Quinoxaline-2-carbaldehydeYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-quinoxalinecarboxylate (10-1) (2.34 g, 11.6 mmol) in tetrahydrofuran (22 mL) was cooled to −78° C. This solution was treated with a 1.0 molar THF solution of lithium aluminum hydride (5.80 mL, 5.80 mmol) added over a period of 6 min. After 30 min, the reaction was quenched with glacial acetic acid (1.30 mL, 22.71 mmol). The reaction mixture was warmed to room temperature and diluted with water (14 mL). The water was extracted five times with ethyl acetate and the combined organics washed with brine and dried (Na2SO4). The solvent was removed in vacuo. Preparative centrifugal TLC (SiO2, 5 mm, CH2Cl2) afforded solid 10-2 (874 mg).

Workup

  1. additionadded over a period of 6 min
  2. extractionThe water was extracted five times with ethyl acetate
  3. washthe combined organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d70998718c7344f8936146ea1a32d04c
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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