Ethyl Acetoacetate → HCID 131732933, compound

HRID 2170227Notes

Reaction equation

HRID 2170227 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]#[N:4].[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:3]([CH:2]([NH:1]/[C:20](/[CH3:22])=[CH:19]/[C:18]([O:24][CH2:25][CH3:26])=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:4]

Participants

6

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 20477989HCID 20477989, compound

Product 1

HCID 131732933HCID 131732933, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of Example 85a (1.063 g, 4.74 mmol), ethyl acetoacetate (0.602 mL, 4.74 mmol), and p-toluenesulfonic acid (0.05 g, 0.263 mmol) in toluene (10 mL) was heated at 80° C. for 4 hours. The reaction mixture was cooled to 0° C. and added to cold saturated NaHCO3. The mixture was extracted with ethyl acetate (2×). The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (1.57 g, 98% yield) which was used without purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×)
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-de9734e536e843e4b6d84bbff296f378
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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