Ethyl Acetoacetate → HCID 70976343, compound

HRID 2170731Notes

Reaction equation

HRID 2170731 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:2]([CH2:19][C:16]2[CH:15]=[CH:14][C:13]([Br:12])=[CH:18][CH:17]=2)([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 70976343HCID 70976343, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl acetoacetate (0.632 mL, 5 mmol) was added to a solution containing NaH (0.493 g, 11.25 mmol) in DMF (5 mL), and the resulting mixture was stirred at 0° C. for 30 minutes. 1-bromo-4-(bromomethyl)benzene (2.788 g, 11.15 mmol) was added to the mixed liquid, and the resulting mixture was stirred at room temperature for 12 hours. The mixed liquid was then poured into a saturated aqueous solution of NaHCO3, and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried using MgSO4, and then concentrated under reduced pressure, yielding the title compound (4k) in a yield of 90%.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated saline solution
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7d09c4e373e4a318d3ed43f0b8dc2ce
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

Loading…