Ethyl Acetoacetate → HCID 24810502, compound

HRID 1919580Notes

Reaction equation

HRID 1919580 reaction equation
CS(O)(=O)=O.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]([NH2:13])=[NH:12].[Cl:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=O.C([O-])(=O)C.[Na+]>C(O)C>[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[NH:13][C:26]([CH3:28])=[C:25]([C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:17]([C:16]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:15]=2[Cl:14])[N:12]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 136381433HCID 136381433, compound

Product 1

HCID 24810502HCID 24810502, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 1H-imidazol-2-formamidine methane sulfonate (Tommasi, R. A., Macchia, W. M., Parker, D. T., Tetrahedron Lett 1998, 39:5947-5950), 2 mmol 2-chloro-4-fluorobenzaldehyde, 2 mmol ethyl acetoacetate and 2.2 mmol sodium acetate were reacted under reflux in 10 ml anhydrous ethanol for 20 hr, concentrated, and then ethyl acetate and water were added to separate the layers. The ethyl acetate layer was dried over anhydrous sodium sulfate, and separated by a column chromatography to obtain 0.19 g of a colorless fine needle crystal with mp 157-162° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.02-1.06 (3H, t, J=7 Hz); 2.43 (3H, s); 3.91-3.93 (2H, m, J=7 Hz); 5.99 (1H, s); 7.04-7.42 (5H, m); 9.59 (1H, s); 12.69 (1H, s); MS (EI) 362.1 (M+).

Workup

  1. concentrationconcentrated
  2. additionethyl acetate and water were added
  3. customto separate the layers
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. customseparated by a column chromatography

Sources & evidence

ORD record
ord-2d5b2d13cf7a4dac8c525e11b57ee9f6
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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