Ethyl Acetoacetate → HCID 21819745, compound

HRID 1654108Notes

Reaction equation

HRID 1654108 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].Br[CH2:13][C:14]([C:16]([F:19])([F:18])[F:17])=[O:15].C(=O)(O)[O-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[CH3:7][C:5]1[O:6][CH2:13][C:14]([OH:15])([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:3]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium Bicarbonate

Product 1

HCID 21819745HCID 21819745, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 18.8 g of sodium hydride in 175 ml of ethanol was added over 3 hours into a mixture of 51 g of ethyl acetoacetate, 74.8 g of 1-bromo-3,3,3-trifluoroacetone and 200 ml of toluene while maintaining a temperature below +10° C. The mixture was stirred for 18 hours and an aqueous sodium bicarbonate solution was added. The mixture was stirred and extracted with isopropyl ether. The extract was dried and the solvent was evaporated to obtain 62 g of the expected product with a boiling point of 64°-72° C.

Workup

  1. temperaturewhile maintaining a temperature below +10° C
  2. stirringThe mixture was stirred
  3. extractionextracted with isopropyl ether
  4. customThe extract was dried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7720e313b9894b3a9ef9d48672006229
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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