Triethylamine → HCID 23438472, compound

HRID 2120088Notes

Reaction equation

HRID 2120088 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C([N:10]([CH2:13][CH3:14])CC)C>C(O)C>[CH:14]1([C:13]2[C:3]([C:2](=[O:7])[CH3:1])=[C:4]([CH3:5])[O:6][N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 31261Acetylacetone

Product 1

HCID 23438472HCID 23438472, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2 and 2,4-pentanedione (0.932 ml, 9.08 mmol) in ethanol (10 ml) was added triethylamine (1.26 ml, 9.08 mmol). The resulting mixture was heated at 70° C. overnight. The reaction was partitioned between EtOAc and water and the layers were separated. The organic layer was dried over sodium sulfate then concentrated in vacuo. The crude product was purified by silica column chromatography (5% to 10% EtOAC:hexanes gradient elution) to afford compound 3 (0.633 g, 3.05 mmol) in 37% yield for 2 steps. 1H NMR (CDCl3) δ 0.8-2.0 (m, 10H), 2.5 (s, 3H), 2.7 (s, 3H), 3.2 (m, 1H).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationthen concentrated in vacuo
  5. customThe crude product was purified by silica column chromatography (5% to 10% EtOAC:hexanes gradient elution)

Sources & evidence

ORD record
ord-528aa722ec22450eb0f89f3417dd2698
Source dataset
uspto-grants-2004_02
Patent number
US06689778B2

Reaction notes

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